Piece two of our history series ended on paper: charters handed to men who had never laid eyes on the land. A link to that article is below in case you missed it or want to go back and refresh your memory.

Eventually somebody had to go and look.

The first permanent settlers reached Wolfeboro in 1768. That same year, a man started clearing land on the shore of what everyone then called Smith’s Pond. He was in his early thirties, born in Portsmouth, governor of the province, and nephew to the Benning Wentworth who signed the charter. He was also one of the original grantees, which made him a rarity: a name on the paper who actually showed up.

John Wentworth built a house there. By most accounts it was enormous, though nobody left plans or a sketch, and it burned in 1820, a couple of decades before photography could have helped. The closest thing to an eyewitness account I have found is a letter from his wife, written in October 1770, the autumn the place was going up around her. She was alone, she told a friend in Portsmouth, and wished someone would come play billiards. The governor was so busy giving directions to his workmen that she had “almost turned hermit.” The great dancing room was nearly finished. She wanted it understood that she did not prefer a grove to a ballroom.

She seems a formidable woman; and one who likely preferred the city to the countryside.

She also mentioned, in passing, the thing that matters most for our story today. She dreaded the trip back to town because “the roads are so bad.”

A house in the woods is a retreat…but only if you can actually reach it. Wentworth lived in Portsmouth, then the seat of government on behalf of the King. Portsmouth, now only about a 35 minute drive, was a long way off by 1770 standards, and he was not going to move a household, a coach, and a ballroom’s worth of guests painstakingly along cow paths through the woods. So he ordered a road, running from Portsmouth up through Rochester toward Wolfeboro. The Wolfeboro Historical Society dates it to 1769, a year after the first permanent settlers in Wolfeboro. The towns along the way were expected to supply the labor, which is where, by the telling of the Rochester historian who has made a study of it, the trouble started.

It helps to know what building a road meant then. Jeremy Belknap, a friend of Wentworth’s who published his history of New Hampshire in 1792, described the method. Surveyors blazed trees and marked each mile. Axemen cleared a strip three rods wide, about fifty feet, and cut the stumps low. Swampy ground got laid over with logs. Small streams were crossed on beaver dams, which Belknap judged firm and convenient. It was, in other words, a road built by neighbors with axes and oxen, and the neighbors had their own farms.

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That July, the New Hampshire Gazette reported that His Excellency had set out for his country seat on Winnipesaukee, and that his lady would follow the next week.

The road he had built, as it happens, runs past my front door.

My house is the Major Jonathan Gilman House, on Governor’s Road in what is now Wakefield. The deed is dated 1769, so the house had just been finished when the road came through and the land it sat on, then several hundred acres, had been granted by the King via Wentworth for services performed by the Gilman family — namely settling the interior. The place was called East Town then, and this was something like the third house built there; the first two belonging to John’s father and brother. The story that goes with it is that the road was laid out to pass the house, and that it served as a staging stop, an inn of sorts, for some of the first travelers. I believe the Governor and his wife stayed here on some of those trips. I can’t prove it. If they did, Lady Frances may have shared her opinions about the roads under my roof, and likely complained about the soup in front of the same fire I now use as ambiance rather than for cooking.

Wentworth himself would sign off on the town’s incorporation as Wakefield five years later, on a petition from the people who lived there, so the man who built the road eventually made the place it ran through official. I keep wondering what all of this looked like from the front step of someone who was staying; the first version of the year-rounder, if you will.

I can tell you some of it, where the historical record, or speculation by historians has provided ideas. In East Town, the first settlers had come in 1766, and the frame of the first meetinghouse went up in 1771 near the outlet of what the records call Lovell’s Pond. Over in Wolfeboro, nine people started farms in the southwest corner of town in 1768, the same year Wentworth began clearing. There were no roads leading in, and most travel ran over the lake. Later county histories say meal came in on men’s shoulders from Gilmanton and Rochester but neither of those towns existed yet, so I imagine Jon and his family were bringing what they couldn’t raise or barter for locally from Portsmouth. They likely would have appreciated the road a bit more than Lady Frances did. The early settlers were poor, it says, and their main capital was muscle.

Into that came a payroll. For three years Wentworth kept a large crew clearing land, planting orchards, laying stone walls, and building a house, with materials hauled by cart and boat from Portsmouth. The bricks for the chimneys are said to have been made at the foot of the falls on Smith’s River. The same county history says the town considered him a benefactor who paid well. It also says that two enslaved people were left behind on his estate when he fled revolutionaries. A later town historian adds that most of the laborers had no plan to stay, and that the estate was close to insolvent, with spending very high and income small. A wage is still a wage when the man paying it is overextended, at least until he leaves.

Then came the guests. In another letter, Lady Frances thanked a friend in Portsmouth for arranging that a house on the road, one the friend herself had lodged at, be made ready for the Wentworths’ return. She wanted it only “a little clean,” she said, because “elegance is not to be found in the country.” I don’t know whose house that was, and I’m not claiming it was mine (though it could have been). But someone kept it, someone made it ready, and I would bet that whoever it was heard some version of that opinion before the visit ended.

What did it mean to the people who stayed? I can only guess, and my guess is that it meant different things in different kitchens. For a family with a spare room, an ox team, or a field of hay, a household that wanted lodging and feed was a market that had not existed the year before. For a town asked to supply labor for a road, it meant owing days of work to a project that mostly served someone else’s route. For anyone who watched the coach go by, it may have meant very little, or it may have meant noticing for the first time that other people thought of this as a place to visit. I doubt any of them thought they were watching the start of anything. Lady Frances herself wrote that winter roads were too uncertain to plan around. The people who lived here had no choice but to plan around them, just like today.

One more thing complicates the tidy version. Seasonal arrival was not only something the wealthy did. Henry Rust, a Portsmouth shipmaster, cleared a lot in Wolfeboro in 1768 with his two sons, farming through the warm months and going back to Portsmouth for winter. One winter the boys, twelve and fourteen, stayed on alone in a log camp with an old horse. His wife did not move up until 1773, in an ox-cart, reluctantly. Rust went on to become the town’s leading citizen. So the line between summer person and settler, at the start, was blurrier than you might assume. It seems to have been less about when you arrived than about whether you made it through a winter and kept going. Again, not unlike today.

The towns were not all thrilled. When Wentworth pushed the road on toward Dartmouth College in 1771, the province appropriated almost nothing to survey sixty or seventy miles of it, and a surveyor’s petition says two lakeside towns ignored the notice to clear their sections. In August 1772 the college’s president wrote to say it was doubtful the road was passable. Wentworth went anyway, with a party of Portsmouth gentlemen. A Dartmouth librarian who spent years tracing the route in the 1920s concluded that it probably never carried wheels before the Revolution, and that it was well suited to the governor’s convenience and not much else.

I would like to tell you the road changed everything. The record is more modest than that. But Brookfield’s own town history credits the road with bringing its first families, who settled along it, and while that account dates the road earlier than the rest of the record does, I believe the instinct behind it. Nobody builds a road for one man and keeps it private. Once it exists, it belongs to whoever uses it.

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Here is what happened next. Wentworth left in 1775, when the province stopped being safe for a royal governor, and he never came back. The state seized the estate and sold it. His house stood another forty-five years and then burned. The road stayed, in pieces. Parts of it are still Governors Road in Rochester and Milton and Sanbornville, and the Governor Wentworth Highway name is on the sign along Route 109 today. The librarian found that after the Revolution, a road survived where it matched what the neighbors needed. Where nobody lived beside it, it went back to brush.

So that is the pattern, as far as I can read it. He said as much himself. In an April 1768 letter he wrote that a country seat was not his only aim, and that he hoped others would follow his example. Money arrives for the season. It builds what it needs to be comfortable. The place rearranges itself, a little, around the result. Wolfeboro’s motto calls it the oldest summer resort in America, and that claim comes down to this one man and this one house.

Not a villain, though. Not a saint either. By every account he loved the woods, he was born here, and he wanted Wolfeboro to be more than a summer address. He once told the Assembly that his salary would not stretch to living in town, which means he described his summer estate to them as a budget measure. He had a long driveway and a lot of neighbors he had not met yet.

Some of you reading this are deciding right now how much of the year to be here. I don’t think that is a moral question. Henry Rust started with summers, too. But it has been a question since 1768, and Wentworth’s road suggests a quiet answer: a place keeps what its people keep open.

If this made you think of someone who loves this region, send it their way.

Here’s to whoever plows the road in March. 🧭

— Jenn

Not nothing. You might just be surprised. A lot of those of us who live here year round have much more active social lives in the fall and winter; which makes sense when you consider that most of us spend the summers joyfully hosting guests. What fills our evenings and weekends once the summer crowd has gone and the boats have been pulled is a handful of rooms that keep the lights on all winter and a handful of bigger ones that book real acts. Here’s my map of both for Oct 15 through Dec 1.

The Regulars

These aren’t events. They’re standing appointments, the kind you don’t put in a calendar because eventually you just know. You’ll start to recognize the same folks if you go to these more than once, which is the universe telling you to make friends.

Wednesdays, 6 to 8, Mr. Sippy’s in Rochester. A bluegrass jam in a barbecue joint, with other artists by invitation on other evenings throughout the winter. You can sit and listen, which is the sensible choice. Or you can bring an instrument and learn exactly where you stand, which is a more educational one. Nobody is cruel about it. The banjo player will simply know. And if you’re lucky, Leanne will be working because she sings one song every Wednesday she’s on and it just might bring tears to your eyes in addition to the smile you’ll break out into.

Saturdays, 3 to 6, Twin Barns in Meredith. Afternoon music through the fall. I’m a fan of the 3 o’clock set, because you get an entire show and still make it home in time to make dinner. That feels like cheating. If they have on it tap when you’re there, don’t sleep on their IPA Palmer’s Town. I don’t even like IPAs and this one is my go to when I’m on that side of the lake.

Saturdays, 6 to 9, Knotty Pine in Sanbornville. Live music at a tavern on Pine River Pond Road. Dinner and a set, in whichever order your appetite votes for. Regulars here will tell you to get here early, because the bar fills up as soon as the sun starts setting. Everything on the menu is solid, but personally I get the baked haddock dinner.

Saturdays, 6 to 8, Hermit Woods in Meredith. Piano in the loft. Reserve a seat. Piano fans plan ahead, which tells you something about piano fans. But you can usually sneak in and still find a seat. Try a wine flight and enjoy an evening of culture and beauty crafted for your palate and for your ears.

Notice what these have in common: a single musician, a room that holds maybe sixty people, and nobody asking you to download anything.

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The Bigger Rooms

Some nights call for a marquee, and there are real ones dotted throughout the area, though you will have to drive for these. Hot tip, in most of these towns there are airbnbs and small inns whose nightly rates are a fraction of what they command during the season. Book a room and make a mini-vacation of it.

At the Flying Monkey in Plymouth, a theater that’s was a regional draw way back during vaudeville and silent film and a very deliberate rescue, the fall runs deep. The Travelin’ McCourys are on Oct 15, Bruce Cockburn and Livingston Taylor on Oct 20, and Gaelic Storm on Oct 25. Later come the Slambovian Circus of Dreams (Nov 14), the James Hunter Six (Nov 19), and Nona’s Supper Club (Nov 21 and 22). One of those names is a band, one is a circus, and one is a dinner. Plymouth contains multitudes.

The Rochester Opera House is another under-appreciated resource that knows how to throw a party you won’t soon forget: Arrested Development on Oct 24, the Artimus Pyle Band on Halloween, an ABBA tribute on Nov 14, and a Billy Joel tribute on Nov 28. I think of Mamma Mania as a nice standing reminder that this region contains a lot of people who will absolutely dance if given the slightest invitation. So, come out dancing queens, and show us your moves.

The Colonial in Laconia has Girls Night: The Musical on Oct 17 and Bat Out of Helloween on Oct 23. Recycled Percussion plays the Cake Theatre in Laconia on Oct 17 and 24, with an afternoon show and an evening show each day. And on Oct 18, the Portland String Quartet is playing with pianist Laura Kargul in the Little White Church in Eaton, which is the sort of sentence that can’t be improved upon no matter the location. Check back later in the fall for The Colonial’s November and December schedule.

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Where to go to make something

Something that has been coming up a lot in conversation as a friend gets The Writers of the Lakes Region up and running is just how much talent there is in this region. And that sentiment is spot on. There are wood workers, jewelry makers, fiber artists, photographers, potters, poets, and memoirists, storytellers, and ceramicists just a stones throw from wherever you find yourself. There’s probably a causal connection with the natural beauty and quiet of this region and how it draws creatives like a magnet, but for now we’ll just call it a correlation. And, most of these folks are really happy to share their talents with you.

Makers Mill in Wolfeboro runs classes nearly every week: printmaking, metalsmithing, mixed media, alcohol inks, leatherwork, sewing, rug braiding. There are free nights too. A Repair Café on the last Sunday of the month lets you bring a broken thing and watch a volunteer fix it, which is a form of theater I like to watch even when I don’t have an item to fix. A fiber arts mingle lets you bring a project and sit with strangers. October is posted. November is on its way, and makersmill.org has the calendar. They give free tours every Friday and the first Saturday of the month.

Hobbs in West Ossipee takes the Hayloft out of the beer-only business: macramé on Oct 22, fall calligraphy on Oct 29, comedy night on Nov 19. A craft class with a beer nearby is the single best idea I can imagine for a fall evening. Grab a friend, or plan to make some new ones, and pop in to learn a new skill.

Artistic Roots in Plymouth is a working gallery, open daily, with a potter, a silversmith, an oil painter, and a woodturner among this month’s featured artists. The Lakes Region Art Association in Tilton rotates exhibits all fall, including a photography show from the Camera Club Oct 15 to 25, and runs adult watercolor workshops on the second and fourth Wednesdays. The League of NH Craftsmen in Meredith teaches small classes, with stained glass candle holders on Oct 17 and 18. And in Campton, Dam Brewhouse has a juried fabric artist on the wall through November, with an artist reception on Monday, Oct 19, from 5 to 6:30.

For anything I’ve missed, lakesregion.org keeps a free events calendar with an arts and culture filter. I’d check a venue’s own page the week you plan to go, because schedules wander. Or, let us all know where you go by leaving a comment.

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Balance is the goal

The marquee shows are fun, and I’ll be there for at least one of them. But the small rooms are the ones that give you something the summer version can’t: the sense that you’re a regular at a place you’ve only been to twice.

A Wednesday jam. A Saturday afternoon set. A printmaking class in a building where the person at the next table is learning too. These aren’t louder or bigger. They’re closer. And closer, it turns out, is what makes me feel like I’m part of something bigger. Community isn’t about an address, its about the conversations you have while learning to make earrings it would have been easier to buy.

If you’re thinking through what community means next, I’m always happy to talk. Even if you’re just thinking out loud.

Here’s to being in the room where the music is made.

🧭Jenn

Keys to the Lakes

Here’s what the law firm framing gets wrong. One of these towns has a general store that tallies your check on a brown paper bag. The other has a barbecue place that closes when the pitmaster decides it’s closed. In one, you pop out for a scone. In the other, you build the quiet on purpose and choose when you’re hanging with your neighbors and when you’re traveling to the rest of the lake for a livelier experience. Same shoreline, same weather, same road connecting these two to each other and to the bigger towns on either side of them. Two very different ideas of what an ordinary Tuesday should feel like.

Tuftonboro: The One You Have to Be In On

Search “things to do in Tuftonboro, NH” and you’ll get a Yelp or TripAdvisor list of things to do in Wolfeboro, Meredith, and North Conway. I’m betting the residents of Tuftonboro don’t mind that at all. It’s also a little funny, because there is plenty going on. Its just an IYKYK type of situation.

Tuftonboro feels like a secret. It has a neighborhood called Hidden Valley, so the town isn’t even trying to be subtle. The best proof is Refuge BBQ and Mercantile, some of the best barbecue in the region. They don’t open every day. The menu is closer to a rumor than a promise. The specials run because the pitmaster feels like it, and when they’re out, they’re out. You can drive over with a plan and come home with a different plan. I love this. I also understand that some people would be less thrilled. That split tells you most of what you need to know about Tuftonboro.

The town publishes a calendar, and it reads like a town that entertains itself. Rug hookers and a cribbage group on Tuesdays. A puzzle group on Fridays, a writers’ group on Saturday mornings, dodgeball on Thursday nights. A hikers’ club with guest-night potluck suppers and programs on subjects ranging from Route 66 to historical preservation. A history book group and a readers’ choice book club. Nearly all of it happens at the free library, which tells you where the center of gravity is.

Then there’s Tuesday night. The Country, Bluegrass and Gospel Music Jam at the Old White Church is the best thing I know of in the Lakes Region that no one puts on a list. I grew up in Nashville, so my standards for a room full of people playing this type of music are not low. This room clears them. People dance in the aisles. Drive by around 7 and you’ll see cars jammed along the side of the road. I’ve heard “take me to church” used as a figure of speech plenty of times. In Tuftonboro every Tuesday, it’s directions.

For daily life in town, the answer is Melvin Village, and for coffee, Pier 19 is your best bet. It’s also a good place to grab groceries if you don’t feel like driving, and I hear the hot food is great, though I haven’t tried it myself. What I can report is that I’m savvily marketed to every time I walk in. I own more than one piece of Lake Winni merch that was clearly meant for tourists and that I absolutely had to have.

The water is the same story as the rest. Mirror Lake and Lower Beech Pond are small lakes with communities built around them, where the only people on the water or the beach are your neighbors. Nobody is performing the lake for visitors, because there aren’t any. It isn’t exclusive. Nobody checks your name at a gate. It’s insider, which is different, and you get in by living there long enough to know.

My shorthand for it is the quiet dorm in college. Everyone in that building chose it on purpose. The party was across the quad and the library was a short walk, and they had decided that they wanted life to be calm and friendly and quiet. In Tuftonboro, you build a quiet life in the middle of everything, and everything is reachable whenever you want it.

What Tuftonboro asks of you is flexibility. It will not organize itself around your schedule. If you need the thing you wanted to be there when you arrive, you’ll be driving to another town when you need that thing. I’ll take the unpredictable barbecue and a bluegrass jam that makes your feet stomp any day of the week.

Moultonborough: The Bridge

Moultonborough holds two things at once without strain. Out on the neck are the big lake homes, the ones that look like they’re about to star in a prestige tv series or host a fashion or design shoot. In town are single and multifamily homes on ordinary streets, the housing a place needs if it wants to stay a town and not turn into a view. Balmoral and Suissevale are good examples of seasonal life here: private associations on Winnipesaukee where some houses look like chalets and the streets have quintessential names that evoke Europe. All of the above is Moultonborough, and no one part of it resents the others as far as I can tell.

What makes it feel like itself is how easy it is to pop out and get something. Cup and Crumb for coffee. Eat the scones. They have plenty of gluten free options, so nobody at the table gets left out. El Mariachi is as authentic a Mexican restaurant as you’ll find in New Hampshire, and I say that as someone who has been let down by the competition. Buckey’s is a great self-proclaimed dive bar, and its sign writer makes me laugh at least once a week. And the Old Country Store is a general store that still tallies your check on a brown paper bag and sells penny candy by the pound. That isn’t a bit. It’s how the store works.

Green’s Corner Market has my household’s second favorite gas station pizza. The first remains Jack’s Pizza in Alton, where I drive to pick up slices instead of ordering whole pies from any freestanding pizzeria. I realize that sentence says something. I’m not quite sure what, other than you can be a snob about food (mea culpa) and not be snobby about where you get the good stuff.

When you want something to do, Moultonborough has a few anchors that are worth the trip for their own sake. Castle in the Clouds, the mountainside estate with the long view back over the lake. The Loon Center, if you want to understand why people up here get so protective about one bird. And when the weather turns, The New Woodshed, cozy fine dining that’s a favorite of mine in winter especially. Start with the French onion soup, then indulge in the rack of lamb, maybe with button mushrooms on the side. The wine list is great, and the room and the regulars do the rest.

What Moultonborough asks of you is a tolerance for not being easily summed up. The neck and the in-town streets are different lives in the same town, and if you want a place you can describe in a sentence, this might not be it. I like that it won’t be put into a box.

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Where They Sit Between the Neighbors

Meredith and Wolfeboro are both wonderful, and I spend a lot of time helping people find home in both. I’m at Harmony Coffee House in Wolfeboro and Mello Moose in Meredith often enough to have opinions on baristas and breakfast sandwich offerings. Both towns have the foot traffic, the downtown you can point at, the energy you can feel from the sidewalk. That’s real.

These two towns that sit between them have access to that energy without living inside it. Moultonborough sits closer to the Meredith side of things, and Tuftonboro leans toward Wolfeboro. You can have the energy when you want it and leave it behind when you don’t. Neither one is a resort town. There’s no season when the town puts on a costume nor one where it takes it off again. The jam fills a church on a Tuesday in February and on one in July, and The New Woodshed is busiest when the lake is frozen but you should call for a reservation in August, too. What each town is on a weekday in the cold is what it is on a Saturday in summer.

The only thing you really give up, by choosing either one over Wolfeboro or Meredith, is the name. Say “I live in Wolfeboro” and people nod. Say “Tuftonboro” and you may get a pause. I’ve decided the pause is a feature.

Pick Your Tuesday

Don’t start with the town. Start with a Tuesday, the ordinary kind with nothing planned. Do you want the coffee shop, the paper bag, and a short list of things within reach? Or a church full of people dancing in the aisles, cars along the road, and a barbecue place that may or may not have brisket? Neither answer is wrong. They’re two different ways of wanting your days to go.

🍁 Jenn

Keys to the Lakes

I did not see this coming, this love affair.

The truth is, bodies of water have never really been my thing. Until this summer, I hadn’t been on a boat other than a ferry or a cruise ship maybe ever. For my entire adult life, and most of my childhood, I lived in cities. We swam in water parks with slides or in public pools. Then, for the 20 years before moving here, I was always within an hour or so of some coast, but one of my most deeply held unpopular opinions is that I hate beach days. I'm perfectly happy to look at the sea, to hear the crash of waves breaking on the beach or rocks, to dine on a pier where the brine in the air matches the brine of the oysters on the plate. But to be on the beach? Feet in the sand? With salt drying on my skin? No thanks. So I knew I would never live on the beach, and even when I fell in love with the Lakes Region and decided I wanted to live here full time, I didn't buy on a lake. And not just because I couldn't afford it (but also).

So something that is a bit surprising to me now is how much I depend on the sight, sounds, and feeling of our lakes, ponds, and marshes. Water here is not one thing, which is the part I couldn’t have explained before feeling the many ways in which it shows up every day here.

I feel a little thrill in my soul every time I come around that corner and first glimpse Lake Wentworth. It matches the thrill I felt when I first drove past it, frozen solid, and marveled at the beauty and at the brave soul careening across it on some sort of wind propelled skimmer craft.

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Lovell Lake is where a good friend has a camp. It’s where the kids and I go for a dip that never requires a plan, and it’s also where I go when something has hold of me, some hurt or fear I can’t get my arms around that day. I don’t always say much. My friend talks, and the lake does the other half. A calm body of water turns out to be a good listener, mostly because it doesn’t try to fix anything.

Winnipesaukee is a different animal. Winnipesaukee is speed and laughter and wind that pulls your hair across your face and takes the words out of your mouth before they reach the ear of whoever is driving the boat. You learn to say less. You learn to mean it with your face instead. And to appreciate how the same landscape can look different from day to day, sometimes moment to moment.

And then there’s the marsh that borders my land, the edge of it creating vernal pools that I get to claim stewardship of. The marsh is part of a watershed that I should probably know the name of, but don’t, and it ties to several streams and maybe a small river that cuts through neighbors properties. My part of it is mostly reeds, and pockets of water; the croak of frogs and the occasional sighting of an owl swooping in for a kill at dusk.

The dogs and I walk down most evenings. We’re making a path, though calling it that is aspirational. It might become a proper walkway someday; right now it’s a negotiation with overgrowth, a weaving under branches and around whatever has decided to grow in the way, until the ground goes soft and we arrive at the mud and the shallow pools. The frogs are loud down there. Loud enough that you stop noticing, and then notice again when something makes them pause. It’s a great spot for bird watching, for communing with oneself, and just generally for recognizing that sometimes a life made of small, quiet moments is just lovely.

I’ve thought about what I’d miss, if I were to suddenly move back to Boston or to some other city around the world. I don’t think it would be the water, itself, first. It would be the lift at the bend in the road. It would be the habit I picked up without noticing, of checking the sky before I check my phone. It would be the particular quiet of standing next to a lake with a friend who has the heart to leave a silence alone.

And the marsh, I think. The mud, the croak of it, the feeling that life is going on all around us in the half dark, whether or not anyone is there to see it. The sense that there is some magic down there, and that it has never once needed me to believe in it. That it preceded me, and will be there long after I’m gone for whomever comes next to discover.

The dogs weave ahead. The pools hold what’s left of the light.

Here’s to discovering what makes your heart lift.

🧭 Jennifer

Keys to the Lakes

Laconia has hosted the pumpkin festival since 2015, when it moved over from Keene, where it had run for twenty-four years. Some places take in a tradition and make it their own. I’m partial to those places.

Something shifts this time of year. The marinas finish hauling boats, weekday parking gets easy again, and the Lakes Region goes back to being a place people live rather than a place people visit. The ones who stayed start running into each other at the same events on the same nights, which is the best part of a small region and the part nobody puts on the brochure.

For myself, its the time of year when I slow down on my drives, sometimes literally gasp in awe at a particularly bright red or orange against a grey sky and act like a tourist and pull over to snap photos of the same places I drive past every day because I can. Here’s one someone else too that captures one of my favorite views in Lincoln, NH.

Here’s a selection from the month. A few of these sit right at the edge of the region, because I draw the borders generously. As always, let me know what I’ve missed by leaving a comment!

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Fairs & Festivals

Mt. Washington Valley Fall Craft Fair, Schouler Park, North Conway. October 2-4. Friday and Saturday, 10 a.m. to 5 p.m., Sunday, 10 a.m. to 4 p.m. A little north of the Lakes Region, but a short drive if you’re on the Carroll County side of things.

Autumn Craft Festival on the Lake, Mill Falls Marketplace, Meredith. Saturday, October 3, 10 a.m. to 6 p.m., and Sunday, October 4, 10 a.m. to 4 p.m. Free, rain or shine. Over 70 juried booths of crafts and specialty foods along the water, now in its 27th year, with leashed dogs welcome and free parking around downtown. A civilized way to start the holiday shopping before anyone is ready to admit that’s what they’re doing.

Antique & Vintage Fair on the Green, Clark Museum Complex, Wolfeboro. Saturday, October 3. Vendors set up on the museum grounds for the last of these fairs this year. Check the Wolfeboro Historical Society for hours.

Sandwich Fair, 7 Wentworth Hill Road, Center Sandwich. October 10-12, Columbus Day weekend. Livestock shows, oxen and tractor pulls, an antique auto show, a parade, a cornhole tournament, a Lego competition, and both a keg toss and a skillet toss, which I would like to see attempted by someone other than me. It tends to land right in peak color. Check thesandwichfair.com for the daily schedule and admission.

The Village at Paugus Bay October Makers Market, 131 Lake Street, Gilford. October 17-18, starting Saturday at 10 a.m. and wrapping Sunday at 3 p.m.

Laconia Pumpkin Festival, downtown Laconia. Friday, October 23, 4 to 10 p.m., and Saturday, October 24, 11 a.m. to 10 p.m. The Friday evening soft opening is new this year, so you get a warm-up. Expect the Runaway Pumpkin 10K and 5K (the course runs past Lake Opechee), the pumpkin tower stacked with glowing jack-o’-lanterns, a kids’ costume parade, a parade of costumed pets, a zombie invasion, food trucks, a beer tent, live music, and laser shows. It is the kind of day you plan around the tower and then end up somewhere near the fried dough. I’ll be there with a booth for Lakes and Peaks Provisions Co. Stop by and say hello.

Haunts & Halloween

Haunted Winnipesaukee, Meredith Town Docks. Thursdays, Fridays, and Saturdays through October 24. Ninety minutes aboard the Winnipesaukee Belle with a Ghost Host, 18 tales of local horror and bizarre history, seasonal desserts, and cocktails made with Tamworth Distillery spirits. It turns out the lake has a darker side, and a bar that makes a mean cocktail.

Fear Farm, Beans & Greens Farm, Gilford. Fridays and Saturdays throughout October, plus Halloween night (Saturday the 31st, 7 to 10 p.m., last entry at 9:30). A woodland trail leads into abandoned greenhouses full of scare actors. Anyone under 18 needs to be with an adult. Not for the faint of heart, or for anyone who has ever been in a greenhouse at night. By day the same farm runs Fall Fun on the Farm, 9 a.m. to 5 p.m.

Happy Hauntings, Story Land, Glen. Weekends through October 25. Trick-or-treating, pumpkin painting, bubble dance parties, and story time with Spookley the Square Pumpkin. Costumes encouraged.

Hocus Pocus, The Flying Monkey, Plymouth. Wednesday, October 14, 6 p.m., doors at 5. The Sanderson sisters on the big screen, with $1 from every ticket going to Pemi-Valley Habitat for Humanity.

The Edgar Allan Poe Afterlife Radio Show, Winnipesaukee Playhouse, Meredith. October 29-31. The Winni Players Community Theatre imagines Poe trying to keep his stories alive from beyond the grave through an otherworldly radio studio and a cast of wandering spirits. The master of the macabre, it seems, has a few things to learn about radio.

Trick or Treat, Clark Museum Complex, Wolfeboro. Saturday, October 31.

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Stage & Gallery

Peter and the Starcatcher, The Colonial Theatre, Laconia. October 9-11. Friday and Saturday at 7:30 p.m., Sunday at 2 p.m. Powerhouse Theatre Collaborative, the same group behind August’s Shrek, is back with the prequel to Peter Pan.

Also at The Colonial Theatre. The Michael Jackson HIStory Show on Wednesday the 14th, Girls Night The Musical on Saturday the 17th, and Bat Out of Helloween, a tribute to Meat Loaf and Rocky Horror, on Friday the 23rd. That last one lands on the same night as the Pumpkin Festival soft opening, which makes Laconia a very full place that evening. Check coloniallaconia.com for times.

Wind & Waves, Lakes Region Art Gallery at the Tanger Outlet, Tilton. New work inspired by the changing light, shifting skies, and seasonal color of a New Hampshire fall. Open daily.

Fundraisers & Community Good

Hops for Habitat, Black Rock Social Club, Portsmouth. Wednesday, October 21, 5 to 7:30 p.m. Portside Real Estate Group’s annual benefit for Habitat for Humanity, done this year in two places on the same night. The Portsmouth side benefits Southeast New Hampshire Habitat for Humanity, and a sister event at Flight Deck Brewing in Brunswick, Maine, benefits Habitat for Humanity 7 Rivers. Food, auction items, and beer, co-hosted by Absolute Title, with 100% of proceeds going to Habitat. Tickets are through the Portside Foundation page. Not the Lakes Region, but an evening on the Seacoast in service of affordable housing is the kind of thing I’m happy to point at.

On the Water & Out on the Land

Castle in the Clouds, Moultonborough. Open daily through October 25, the last day of the 2026 season. Lake views, daily tours of Lucknow Mansion, and a new exhibition, “From Private Estate to Public Treasure: Lucknow after Thomas and Olive Plant.” On Friday, October 2, the head gardener leads a Lucknow Garden Tour from 10 to 11:30 a.m.

Squam Lakes Natural Science Center, Holderness. Last call for pontoon season. Cruise with a Naturalist runs Wednesdays and Thursdays at 3 p.m. through October 8, and the Discover Squam guided cruise runs daily, 1 to 2:30 p.m., through October 12. The Live Animal Exhibit Trail stays open daily through November 1.

Weekly Rituals

Tilt’n Diner Cruise Night, Tilton. Thursdays, 5 to 7 p.m., classic cars out front. The final one is October 29.

Thursty Thursdays, Notch Biergarten at Beans & Greens Farm, Gilford. Thursdays from 5 p.m. Live music, table and yard games.

Live Music on the Patio, Hermit Woods Winery, Meredith. Fridays, 5 to 8 p.m., and Saturdays, noon to 3 p.m., rain or shine. They move inside if the weather turns.

Farmers’ markets. Weirs Community Park in Laconia, Saturdays, 10 a.m. to 1 p.m., through October 3. Barnstead, Saturdays, 10 a.m. to 1 p.m., through October 10. The last weekends of the season for both.

Free First Friday, The Belknap Mill, Laconia. Friday, October 2, free museum admission, 10 a.m. to 4 p.m.

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Anytime in October

Apple picking is still on at Surowiec Farm in Sanbornton and at Stone Mountain Farm and Smith Orchard in Belmont, though hours thin out as the month goes on, so check before you drive.

October doesn’t wait for you to be ready for it. The color comes in when it comes in, the fairs happen on the weekends they’ve always happened, and the light goes early now, early enough to catch you off guard in a parking lot. Here’s to the last warm afternoon, the first fire in the stove, and whatever you end up holding at the pumpkin tower.

🧭 Jennifer
Keys to the Lakes

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So let me answer it plainly.

If I could change one thing about leaving Boston Metro, it isn’t the takeout, really; though long time readers know how I feel about the lack of access to Bhindi Masala and Injera. It’s specialist access. That’s the real trade. For the ordinary stuff, the sprained ankle, the flu, the stitches, you’re fine. Wolfeboro has a hospital. Plymouth has a hospital. Dover has a hospital, all solid, all staffed, all capable of handling what most people need on most days. But the minute you need a specialist, a particular kind of cardiologist, a rheumatologist, anything requiring a subspecialty and a waiting list, you’re probably opting to drive. Portland. Portsmouth. Manchester. Or Boston, which is where most of my neighbors end up when it’s something serious. And, its where we still drive every three months to see the Endocrinologist who’s treated a family members Type 1 Diabetes for the last 10 years.

The ambulance response times in the more rural corners of this region come up at kitchen tables more than you’d think, and access to ongoing mental health care, especially for younger people navigating something complicated, is thinner here than in a city with a hospital system on every corner. Also worth naming is that most people working with me on a third-chapter move aren’t raising teenagers here, so that particular gap, real as it is, isn’t the center of this decision for most of my clients; though it does come up at times.

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For the people this piece is speaking to, though, the calculus is different. It’s not “can I get to a hospital.” You can, and you have choices. The underlying question often turns out to be, “will I still feel like myself here,” and that’s where the story is actually a really good one.

Start with food, because it is a rural trope for a reason. You’ll pay more at the farmers markets than you will at Hannaford or Market Basket, no argument there, but the range is the part people don’t always expect. Produce, dairy, eggs, meat, all of it available direct from the people who raised or grew it, and once you know the rhythm of who sells what and when, you could conceivably go an without setting foot in a supermarket, unless you need orange powder mac and cheese (no judgement, we eat a lot of it at our house) or a specific spice or something wrapped in plastic with a barcode. That’s not a romantic exaggeration. That’s just how the sourcing works once you build the habit.

Fitness is its own strong case, and it’s not the one gym in one town people picture when they imagine rural New England. There’s a real gym within twenty minutes of almost anywhere in the Lakes Region, and on top of that, classes happening constantly in places you wouldn’t think to look. Town halls. Libraries. School gyms after hours. Yoga studios that run out of a converted barn or a storefront on Main Street. The infrastructure is distributed rather than centralized, which means you’re rarely more than a short drive from something.

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And then there’s everything that isn’t a class at all, just the region doing what it does. Ski at Abenaki or Gunstock. Swim almost anywhere the shore touches water. Snowshoe or hike depending on the season, run if that’s your thing, kayak when the lake’s calm enough to make it look easy. What strikes me isn’t just that the activities exist, it’s how many people are already doing them, in every town, which means you’re rarely doing any of it alone unless you want to be.

I had a good example of this on Friday. I was at my knitting circle, and there was about as much talk happening as knitting. The hostess looked down at her watch mid-sentence and gasped, “ladies, we have to wrap this up, three of us have to get over to the Nick for pickleball in ten minutes.” That’s the texture of it. Nobody’s schedule up here has room to be lonely even if they wanted one.

Often when pundit talk about the loneliness epidemic, the advice offered is abstract. Join a group. Build community. Put yourself out there. What actually happens here is less deliberate than that. You go for a walk on the rail trail to move your body and come home having had three conversations with people you didn’t plan on talking to. You join a knitting circle for the knitting and end up double-booked for pickleball. You pop by the farmers market to pick up some peppers and end up agreeing to help herd some pigs into their enclosure later that day. The third-chapter people I actually know up here read as unusually well-connected, not because they worked at it, but because the region makes isolation a choice you can make if you want, not a foregone conclusion.

Behind all of it sits infrastructure most people never think to ask about: town senior centers doing the steady, unglamorous work of running programs week after week, and regional senior organizations stitching those towns together so nobody’s cut off just because their particular town is small.

So that’s the honest read, both halves of it. The medical side asks you to accept a real tradeoff. The fitness and social side hands you something back that’s harder to put a price on, and for most of the people reading this, it isn’t a close call which one weighs more.

Here’s to knowing what you’re actually getting and what you really want.

🧭 Jenn

Keys to the Lakes

This is part of an ongoing series about what the third chapter of life actually looks like in the Lakes Region, for the people who chose it.

On my walk along the dock to get here, I passed guys already pulling boats. Not all of them. Just enough.

45 minutes down the road, back home, that’s not an occasional thing anymore. It’s daily. I either see it happening in person, boats coming out, getting shrink wrapped, trailered off toward someone’s barn or a storage lot, or I see it secondhand, in the wave of Facebook posts. Last sail of the season. Until next year. Somebody always adds a sunset photo.

Nobody up here needs the leaves to tell them the season’s turning. The boats do it first.

I used to think of that as a closing sound. The hum of a shrink-wrap gun, plastic going taut in the wind. But I’ve come around on it, because I know exactly what comes next, and it’s not quiet.

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The Lakes Region Newcomers Club starts scheduling its Mix and Mingles again, and if you don’t sign up within the first hour of one going up, you’ve missed it. I’m on the waitlist for October’s, which is happening at The New Woodshed, a place I love most in fall and winter, when the massive fireplace is doing real work and the light through the windows turns everything the color of the season. Last year, at that same Mix and Mingle, I ended up at a table with people who became the friends that brought laughter and long lunches to my life all winter long. I still think about the conversation from that one night, about what it actually looks like to be someone who chooses to winter over here instead of heading to Florida or South Carolina or Texas the way so many people do the second it gets cold. It’s a different kind of person who makes that choice. If you’ve been enjoying the series about what retirement looks like in the Lakes Region, in its many forms, thank the folks sitting at that table; they were the inspiration.

The special interest groups fill back in too. Coffee Klatch, Lunch Bunch, the Creative Writing group I co-lead, Enquiring Minds, all of it revving back up now that the summer people have thinned out. I can walk into pretty much any restaurant in town, as long as it’s still open for the season, and actually get a seat at the bar or a table without waiting. That alone feels like a small luxury after a summer of elbow room.

There’s apple picking coming, cider donuts, and the Laconia Pumpkin Festival, which is less a festival and more a street party built around a wall of carved jack-o-lanterns that goes up something like 40 feet high. It’s a genuinely strange thing to stand in front of. Raucous, a little absurd, and more fun than a wall of pumpkins has any right to be.

And the neighbor emails start up again, the ones that say something like, now that things are quieting down, want to do a bonfire, or a supper on the porch, or drinks while we watch the leaves turn. Those emails don’t happen in July. Everyone’s too busy being busy.

So yes, my swimming’s probably done for the year, unless we get one of those freak warm pockets in October that fools everybody into thinking summer forgot something. Kayaking too. But I’ve written about this before and I’ll keep writing about it, because it keeps proving itself true: the shift from summer busy to locals busy isn’t a slowdown. It’s a different shape of full.

That’s what a real year-round community looks like. It doesn’t go dormant when the tourists stay home. It just changes what’s on the calendar, and honestly, changes who’s at the table. This is the season when you find out who your actual neighbors are, the ones still here in January, the ones who send the bonfire email instead of the Florida postcard.

The boats will all be out of the water soon. Every last one. And this place will still be exactly this busy, just indoors, and closer together, and dare I say with absolutely scintillating conversation.

Here’s to the season that starts when the boats come out.

🧭 Jennifer

Keys to the Lakes

And, just like that, what used to be pretty rare happened twice in 90 minutes. It was basically what sellers have been doing all summer, condensed into two phone calls.

After nearly a decade of prices only moving in one direction, sellers are recalibrating, publicly and sometimes uncomfortably. I want to be clear that this isn’t a collapse. No doomsday headlines or fearmongering here, folks. Most of these sellers, especially anyone who bought before 2020, are still going to walk away from closing with more money than they put in, by a lot. But the number they had in their head, the one from last year, or from their neighbor’s sale in 2022, or from the appraisal during the refinance boom, isn’t the number anymore. And I don’t think it’s just sellers carrying around an outdated figure. Buyers are too. And, there’s an actively shifting conversation around interest rates, which I want to actually take apart, because I think it’s doing more to freeze people in place than the rate itself.

So, here’s a sentence I hardly ever write here, or anywhere. Let’s do some math! Here’s some nature, first, because I’ve found that numbers stress people out and nature does the opposite.

The rate isn’t the problem you think it is

That’s right, I’m saying it. Seven percent is not a calamity. Let’s do the math together. The thirty year fixed has been sitting close to seven percent this fall, up from the mid sixes for most of the last year. On a loan of four hundred fifty thousand dollars, the difference between six and a half percent and seven percent is around a hundred fifty dollars a month. That’s real money, I know. It’s also less than a lot of households spend on groceries every week, and it’s being treated like a wall instead of a line item.

Meanwhile, close to thirty percent of home purchases nationally are still happening in cash, no mortgage, no rate conversation at all. That share was closer to thirty five percent when rates were flirting with eight percent a couple years back, which tells you something: cash buyers show up in bigger numbers exactly when financing gets expensive, because for a real slice of the market, the rate was never the actual obstacle. It’s a signal. A lot of buyers are reading it as a flashing yellow caution light. A lot of others are reading it as a stop sign.

What about first time home buyers? Rent isn’t free either, but I definitely remember feeling like the known of my monthly rent was less overwhelming that thinking about mortgages and insurance and taxes and etc.. So let’s actually run a real comparison, because the version of this story people tell each other at dinner parties usually isn’t the real one.

Say you’re renting a two bedroom in Dover, paying somewhere around $2200 a month, which is about where that market sits right now. Say you qualify for a first time buyer loan, five percent down, and you’re preapproved for $500,000. Here’s the actual math, not the rounded down version. That’s a $475,000 dollar loan. At today’s rate, principal and interest alone runs around $3160 a month. Add property tax at New Hampshire’s average effective rate, another $750. Add insurance, call it $125. Add the mortgage insurance that comes standard with five percent down, another $275-$300. You land around $4300 a month. The gap between renting and buying is not insignificant.

I’d rather you know that than find it out on your first mortgage statement.

Here’s the equity side, run the same honest way. Two years in, you’ve paid down roughly $10,000 in principal. If the home appreciates at something like three percent a year, which is closer to what’s actually being forecast right now than the double digit years everyone still has stuck in their head, that’s another $30,000 or so in value. Sell at that point, pay a commission and closing costs, and you are not clearing $200,000. You’re close to breaking even against what you spent to own instead of rent, once you count the down payment and that extra $2200 monthly premium.

That’s the two year story, and it’s not a great one. But buying a house was never a two year decision, at least not until COVID. Which brings me to the couple I keep thinking about, because they didn’t get rich in year two either.

Say you bought a house here for $200,000 back in 2018, financed most of it at a rate that was, for what it’s worth, still north of four percent. That house is worth something in the neighborhood of $800,000 this fall. After paying off what’s left on the mortgage and covering the cost of selling, you’re walking away with something like $600,000. The math only worked because they stayed seven or eight years, long enough for the rent they would have paid instead to keep climbing the whole time, and long enough for appreciation and principal paydown to actually compound. So the honest version of “should you keep renting” isn’t a two year pitch. It’s a horizon question. Are you staying long enough for the math to do what everyone assumes it already does the moment you sign.

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What “the market” actually means here

This is where I have to complicate things further, because “the Lakes Region market” isn’t one market. It’s several, wearing the same zip codes.

Right now, year round three and four bedroom homes between $400,000 and $650,000, the ones that don’t need a full gut before you can live in them, are moving quickly. That segment is carrying the region.

Waterfront on Winnipesaukee is its own animal, and it always has been. This year the median sale price on the lake was north of two million dollars, and those homes are sitting on the market more than four times longer than the region’s overall median. That’s not weakness, waterfront buyers move at their own pace, but it does mean “the market is hot” and “the market is slow” are frequently two people talking about two completely different products.

And then there’s the segment I think is most interesting: entry level and mid priced homes that need real work. A house priced at $450,000 that needs a new kitchen, new systems, maybe a full gut, is sitting. Not because buyers can’t afford $450,000. Because they can’t wrap their head around spending half a million and then writing a second, uncapped check to a contractor. That’s not a financing problem or an inventory problem, that’s a psychological one, and I don’t think the market conversation accounts for it nearly enough.

So the real answer to “is it a buyer’s market” isn’t yes or no. It’s which segment are you actually in.

What I don’t fully know yet: the Seacoast

I want to be honest about the fact that I’m newer to advising on the Seacoast than I am the Lakes Region, and I’d rather say that plainly than pretend otherwise. But the data tells the same “it depends” story in a different accent, and it’s worth laying out.

Single family homes there are still the most competitive piece of the market, well priced ones moving in under three weeks. Condos, especially waterfront units, run closer to a month and a half, strong demand, just a different pace. The luxury tier looks like our waterfront story in miniature, more patience required, closer to six weeks on market, buyers who aren’t in a hurry. And investment buyers are playing an entirely different game, they’re not chasing Portsmouth waterfront, they’re buying two and three unit properties in Rochester, Somersworth, and the Dover outskirts where the numbers still work. Vacancy along that corridor is sitting near four percent against a national average closer to seven, which tells you rental demand isn’t going anywhere.

Same complicated answer as the Lakes Region. Different air.

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What this actually means if you’re deciding right now

If you’re a buyer who’s been sitting out because of the rate, run your own numbers instead of the headline. A hundred fifty dollars a month might change your answer. It might not, once you put it next to what you’re already paying in rent, or what another year of waiting might do to the price of the house you actually want, or how long you actually plan to stay once you buy it.

If you’re a seller holding onto a number from a year or two ago, I understand why. It’s hard to let go of a figure once you’ve said it out loud to your spouse, your kids, yourself. But the two calls I got today are the market telling you, gently, that the number has moved. You’re probably still going to do very well. Just maybe not at the number you were picturing.

If you’re thinking through what any of this means for you, I’m always happy to talk. Even if you’re just thinking out loud.

Here’s to running your own math instead of making decisions based on someone else’s headline.

🧭 Jennifer

Keys to the Lakes

Nobody around here can agree on what’s happening this year, in ways that go beyond the weather. That’s the real story, more than any of it being early or late or right on time. People aren’t sure if they should pull the boats out, move from Camp to wherever their winter home is, or depend on the unpredictability of it all and just wait and see.

I met a friend and client who recently closed on a new home on the patio at El Centenario where we shivered but stubbornly insisted that margaritas on a patio in September was a no brainer. He told me, with the specific confidence of someone who has just made a tactical error, that he’d taken his window units out for the season. Which means, by local lore, we are now owed a heat wave sometime before Columbus Day. And, when I say that, I’m joking (and so was he), but only sort of. It’s closer to a genuine hedge, the kind everyone in this region makes without noticing they’re doing it. Summer flew by faster than usual, we say. Feels like an early fall, we say. And then we immediately protect ourselves from being wrong about it.

I keep thinking about a party I threw two Octobers ago, when everyone ended up drifting into the back garden, fairy lights strung along the fence, grass still high enough to catch on your ankles, everybody in short sleeves like it was the summer solstice instead of Halloween. That night is in the same folder in my head as this afternoon’s rain and blanket and closed window, even though the only thing they have in common is that they failed to understand the assignment. That’s what a Lakes Region fall actually is. Not a season so much as a folder full of contradictory signals.

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I was in Portsmouth for lunch today, a mere 40 minutes south, to talk to a new client about listing their seacoast home of 20 years and the story didn’t change so much as resonate in a different key. The host at the restaurant had on one of those Irish fisherman’s sweaters. The late-summer tourists were out in shorts, hustling along sidewalks that had gone slick with rain, looking like people who’d read a different forecast than the one actually happening around them. Same uncertainty, same collective shrug, just with an urban harbor view instead of a country lake one.

The brochure version of fall up here is a single, iconic image, that’s been sold so consistently that most people can picture it whether they’ve ever visited in person or not. A ridgeline gone orange and yellow and red as far as the eye can see. A red barn with pumpkins stacked on the porch. Somebody’s grandmother’s hands wrapped around a mug of cider, steam catching the light just right. It’s the version on the postcard rack at the general store, the version a hundred Instagram accounts recreate at the same three overlooks every year, the version that shows up in every “best fall foliage towns” listicle with a stock photo that could be any covered bridge in New England. And I want to be clear that it’s not fake. That weekend exists. I have escorted guests across said covered bridge in a flannel with a hot cider in one hand and an apple donut in the other, leaves crunching satisfyingly under my feet. I’ve grinned as I sped past tourists pulled over on the shoulder with their hazards on, taking the same photo everyone before them has taken. And I can’t even blame them for it.

What the brochure obscures is that these are all moments, not a season, and which weekend gives you the promised experience changes every year depending on things nobody around here controls. An early frost or an early nor’easter can strip a ridge to bare branches before the leaf peepers even book their rooms. A wet, warm September can hold the green on for so long that color doesn’t really arrive until people have already given up and gone home. A summer that does an early Irish goodbye, the way this one has, can shove the whole thing sideways so that what should be six weeks of gradual turning collapses into ten unpredictable days. The postcard has the luxury of capturing the Platonic ideal of fall in New Hampshire. Living here means you get whatever outcome actually shows up, and you don’t get a vote.

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I don't think that's a flaw in the place. I think it's closer to the actual character of it. You stop checking the forecast so much as reading the room, the way my friend reads the nights to decide when to pull the window units, the way I read the apples dropping off that tree. You start keeping a lap blanket by your desk in September, just in case, even though your shorts and bathing suits are still in the dresser. And there's every chance this year could be the kind that hands you a need for both in the same month. Who knows?

Here’s what I do know. I’m definitely going to buy the cider donuts this year just like I do every fall. I just won’t pretend I know when.

Here’s to the version of autumn that actually shows up, not the one on the postcard.

🧭 Jennifer

Keys to the Lakes

I asked him the obvious question, the one anyone who came from a place with a paid fire department would ask, which is basically: wait, so who’s actually coming? And he laughed a little, the way you laugh when you’ve explained something a hundred times to people who’ve never had to think about it, and told me how this works out here. How there’s a combination of professional fire fighters and EMTs and how most of those are supplemented by incredibly generous volunteers. He taught me about mutual aid, how when there’s an emergency in one town, say Wakefield, the call goes out to Wolfeboro, or Ossipee, or Moultonborough, whoever’s closest and free. Towns covering towns. Neighbors covering neighbors, some of whom have never met, showing up in each other’s driveways in the middle of the night because that’s simply how the system is built.

I’ve lived here three years and I’ve never thought about any of this. Not because I didn’t care. Because I’d never needed to.

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That’s the thing about this kind of infrastructure. It’s not a backup system, and it’s not a stopgap until the town can afford something better. It is the system, in a lot of these towns, and it runs almost entirely on people who decided, at some point, to show up for something nobody was making them show up for.

I noticed the same shape again this morning, half by accident. I was standing in line at the pharmacy with my fellow Wolfeboro denizens (IYKYK), scrolling to pass the time, and I got pulled into an article about a local conservation group tracking invasive plant species across the lakes here. Milfoil, mostly, the kind of thing that can choke a lake if nobody catches it early. What stopped me wasn’t the science. It was realizing the people doing it are almost entirely volunteers. People in kayaks with clipboards, mapping plant beds lake by lake, paying particular attention to the ones that cross into Maine or connect by river, because a species that shows up in one body of water can travel to the next one if nobody’s watching the door. Nobody is paying them to notice this. They notice it because if they don’t, nobody will, and then it’s a problem that costs real money and takes years to undo.

And then I remembered a few days ago, I was having lunch with my friend Diane, who sells real estate the way I do - with a deep love for this place, and she started telling me about the food pantry she spends time at. Not fundraises for. Volunteers at. Stocks shelves, knows which families are stretched thinner some months than others, does the quiet math of who needs what and doesn’t make it a production. She talked about it the way you’d talk about something completely ordinary, which is its own kind of tell. For her, it is ordinary. It’s just what Thursdays sometimes look like.

Three conversations, three days, none of them related, and I kept noticing the same architecture underneath. A fire department. A conservation effort. A food pantry. None of them staffed the way you’d assume, if you came from somewhere with a robust non-profit system or the type of government funding that major cities like Boston can provide.

I do a version of this myself, though I want to be honest about the scale of it. I show up for the Lakes Region Board of Realtors beach and park cleanups in the spring. I do the shuffles for the Children’s Auction. I go to the Kingswood Youth Center’s chili cookoff and buy more raffle tickets than any one person needs. My brokerage, Portside Real Estate Group, has an Autumn Equinox fundraiser over at Maine Audubon next week, and I’ll be there for that too. None of that is the same as a two a.m. page, and I’m not going to dress it up like it is. But it’s the same instinct, scaled to what I actually have to give, which I think is closer to how most people end up in this economy than the volunteer firefighter version. You don’t have to be him to be part of it. You just have to be someone who shows up for something.

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Here’s what I keep landing on, though. This isn’t a formality. It’s a filter.

You can live here for years, buy the house, get the plates, learn which road doesn’t get plowed in January, and still be a tourist in a lot of ways, if you never once show up for anything that wasn’t about you. Meanwhile the person who’s been here six months but joined the conservation commission, or started pulling shifts at the food pantry, or just consistently turns up to the things that need turning up for, is already rooted here. And its not that anyone is keeping score; the whole idea of mutual aid is that we all have something we can give and we all have something we need. Rootedness here isn’t about duration; it’s about participation. This place doesn’t run on being present. It runs on people deciding, repeatedly, to be useful.

I don’t think anyone should join a board because I said so in a newsletter. That’s not the point of any of this, and honestly it would be a strange thing for me to push, given that my own contribution mostly involves raffle tickets and beach cleanups. I just think it’s worth naming, because if you’re like me even though you want to give back, you just might not have been thinking about it all that much. Nobody puts in the listing, “two car garage, new HVAC, volunteer position as a literacy tutor at your local library.” You find out the fire department runs on volunteers the night you need them, or you find out some other way, over dinner, next to a neighbor who explains it to you like it’s the most obvious thing in the world. Which, out here, it is.

Here’s to the people who show up.

🧭 Jennifer

Keys to the Lakes

I watch this happen every fall. Not everyone who owns a lake or ski property is ready to sell. Most folks will tell you they held on longer than they probably should have. But every September, a specific kind of owner makes a specific kind of decision, and it has nothing to do with the market and everything to do with a summer that felt different than the one before it. Fewer weekends up. A kid who’d rather be somewhere else. A knee that doesn’t love the dock stairs anymore. They spend the season quietly deciding, and by the time the leaves start to turn, they’re ready to list.

This is not the moment most buyers are watching. Everyone tends to think that spring is the best time to shop, when the water’s blue in the listing photos and the summer season is coming up. Which is exactly why fall and winter are the better window if you’re buying for investment, not for your own Saturday afternoons. The owners listing now aren’t testing the market. They’ve already made peace with leaving. That tends to mean more room to negotiate, and properties that show up honestly rather than staged for a July daydream.

There’s a second piece of timing here that’s easy to miss if you’re only thinking about lake season. A property that only works in July is a property that sits empty eight months a year. A property that works for both ski season and lake season doesn’t. The Lakes Region has more of these than people realize, towns close enough to a mountain and a shoreline that a renter booking a February weekend and a renter booking a July week are looking at the same house.

There’s a broader reason this kind of buy makes sense right now, and it has nothing to do with New Hampshire specifically. Open any financial news this year and you’ll find the same unsettled tone, rates that keep everyone guessing, a bond market that seems to have a strong opinion about something new every week, headlines that don’t leave a lot of people feeling steady. I’m not going to pretend to know which of those headlines matters most. What I do know is that a house on a lake, in a town people already plan their year around visiting, doesn’t behave like a ticker. It doesn’t drop eight percent on a Tuesday because of something that happened somewhere else. People still want a week at the lake in July and a weekend near the mountain in February whether the market’s up or down, and often want it more when everything else feels unsteady and they need somewhere to actually stand still and just breathe.

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That’s the case for an asset you can also sleep in. It holds value the way land and water tend to, slowly and without much drama, regardless of what’s happening in a boardroom somewhere. New Hampshire helps too. No income tax, no sales tax, which compounds the longer you hold something. This is a bet on the fact that people have been coming to this region for generations, and a well-chosen property here works for you in more ways than the market ever will.

I pulled together five properties, all under $900,000, all offering something closer to year-round rentability than a single-season one. I looked at price, at proximity to both water and skiing, and, because this matters more than most buyers realize until they’re three months into ownership, at what each town actually allows.

325 Belknap Mountain Road, Gilford — $850,000. Four bedrooms, three baths, sitting across from conservation land with hiking trails right out the door. Gilford residents get exclusive access to Gilford Beach and the town docks on Winnipesaukee, and the town is home to Gunstock, so this is as close to true dual-season as it gets without qualification. Gilford requires a Conditional Use Permit for short-term rentals, a real but well-worn process. Forty-six days on market, which tells me the owner decided early in the season that they’re ready to move on to the next adventure.

6 Sunset Lane, Moultonborough — $775,000. Three bedrooms in Swallow Point, water views from nearly every room, west-facing sunsets, association access to the lake. The listing itself states no rental restrictions, and says plainly that it works as an investment property with income potential. I’d still call the town before closing, since Moultonborough doesn’t have a dedicated short-term rental ordinance on the books and the planning board has been actively sorting out how to formalize what’s currently handled informally. Worth the phone call. It hasn’t stopped this owner from marketing it as exactly that kind of property.

39 Captain Lovewell Lane, Ossipee — $638,984. The lowest entry point in the group, three bedrooms sitting on the Indian Mound Golf Course with association access to Ossipee Lake’s beach. Golfers in the morning, lake in the afternoon, and it’s close enough to the King Pine corridor to pull winter bookings too. Ossipee’s short-term rental ordinance permits rentals in all districts with a business license from the Board of Selectmen, one of the more straightforward paths on this list.

300 Mill Brook Road, Thornton — $739,000. Three bedrooms, brookside, sitting almost exactly between Waterville Valley, Plymouth, and Lincoln. This is the one that leans hardest into ski season without giving up water entirely, two hundred feet of exclusively owned brook frontage and a wall of south-facing windows built for winter light. Thornton permits short-term rentals in every zoning district, and this one comes with a new roof and a fifty-year warranty, which matters more than people think when they’re running the numbers on a rental.

257 Meredith Neck Road, Meredith — $899,000. The biggest of the five, five bedrooms and nearly four thousand square feet on 2.47 private acres a few minutes from downtown Meredith. This is also a property with a short-term rental track record. It’s already been operated that way, with what the listing calls a proven history of guest demand. Meredith allows short-term rentals as an accessory use by special exception, and this house is the proof that the process works in practice, not just on paper.

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That last point is worth sitting with for a second. Every one of these towns treats short-term rentals differently, and the difference isn’t a formality. It’s the line between a property that pays for itself and one that sits vacant while you fight a zoning board. I did the homework on all five of these before I put them in front of you, but that homework has an expiration date. Ordinances shift. Special exceptions get revisited. Before anyone gets attached to a listing photo, the town office is worth a call.

The market’s telling you something right now, if you’re paying attention to the right signal. Not the listing price. The season the owner just finished.

If you know someone who just wrapped their last season and hasn't said so out loud yet, I'd be glad to talk with them, no pressure, no pitch. And if you've been quietly running the numbers on whether a short-term rental belongs in your own portfolio, I'm around for that conversation too.

Here’s to knowing when to play the long game.

🧭 Jenn

Keys to the Lakes

So, imagine it’s a Tuesday in March, a little after seven a.m., and the diner has four people in it besides me. Not just four customers. Four regulars, which is a different category entirely. One of them is arguing with the woman behind the counter about whether the plow crew missed his road on purpose. She’s not taking the bait. She’s also already pouring his coffee without asking, because at this point asking would be an insult.

This diner closes at two. That’s not a failure of the place, it’s just the shape of the day here. If you want something to eat or drink after that, you’re headed to the pub, because the two of them split the day between them without ever discussing it. Somewhere in this town is open from six in the morning until eight at night. But it’s not the same somewhere.

Across the lot, the hardware store hasn’t opened yet, but there’s a truck already backed up to the feed store loading door and a guy in Carhartts leaning against it, waiting, in no apparent hurry. Nobody’s in a hurry here in March. That’s kind of the point.

This is not a postcard moment. Nothing about it is trying to be seen. The snowbanks are the gray, gritted, end-of-winter kind. The flag outside the fire station is a little tattered. But from mid-October to mid-May, this is the day to day picture of the town. It’s not boats and fireworks; its waves from across the street as you dash into the gas station and its figuring out which of your neighbors to talk politics with over a pint and which to stick to conversations about music and dogs and books.

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And it’s a pretty good test, I think. Not what a town looks like in September. What it looks like in March.

Here’s what I don’t think is true, though I used to believe it: that some towns are open all year and some towns roll up the sidewalks in October. That’s not how it actually works. Every town up here behaves differently in January than it does in July, and there isn’t a single one that’s fully itself in both seasons at once. What’s actually true is smaller and more interesting than that. Every town has something. Only a few have all the things. And which few keeps shifting, year over year, one storefront at a time.

A decade ago, a lot of the Main Streets around here had those hand-lettered signs in the window every October. See you next season. Some of that has quietly shifted, not because anyone ran a campaign about it, but because enough year-round people decided they didn’t want to drive forty minutes for dinner every time they wanted someone else to cook, and enough business owners noticed and stayed open to meet that demand. But almost every town has at least one with closed for the season taped in the window, and some towns have a lot more than one. But that’s okay. Those aren’t the stores locals were ever walking into. They’re selling sweatshirts with the lake’s name across the chest and wall art about lake life to people who are here for eleven days a year, and that’s a real and legitimate part of how this economy holds together. Nobody who lives here in March needs a sweatshirt that says the lake on it. We’ve already got the sweatshirt from the high school up the road, and the mug we may or may not have “accidentally” walked out of the diner with.

So it isn’t really a have-it-or-don’t binary. It’s more of a spectrum where all the towns have something to offer and some have more this or less of that. Some people have chosen the town where there are five real places to eat in January, every night of the week. Some have chosen the one where it’s the diner in the morning, the pub after two, and the market for whatever’s in between, and that’s enough. And some have chosen the town where none of that is in walking distance, where it’s a twenty-minute drive to any of it, but the twenty minutes is a known and reliable cost, not a maybe. All three are legitimate ways to live here. They’re just different bets about what you want close enough to encounter every day.

Here’s some of what I decided that I wanted, which could be different from what you would choose.

A hardware store that still sells things by the individual bolt, and the guy behind the counter can tell you which one you need without you fully explaining the project. Where you can get chicken feed and a toilet plunger and snow shovel or a lawn mower and spring vegetable seeds and string lights.

A library that’s doing more than holding books. The room in the back where the writers’ group meets on Tuesdays, the folding chairs that come out for a concert nobody paid a ticket to see, the sheet hung up for a movie night in a town too small to have its own theater.

A fire department that isn’t volunteer anymore in most of these towns, it’s professional now, but it’s stretched across two or three towns at once, running on a mutual aid system that assumes your town’s rig might be the one that shows up first in the next town over, and vice versa, without anybody making a thing of it.

A local market where they know you by your third visit, not because you’re memorable, but because your kid worked the register there the summer they turned fifteen, same as half the other kids in town did before him, and because you’re in for chips and coffee and dog food on a Wednesday, the kind of errand that will never justify the twenty-minute drive to the real supermarket.

None of this is about charm. Charm is easy to manufacture and easy to fake for a season. This is about infrastructure. Actual, unglamorous, keep-the-place-running infrastructure, built by people who live here in February, not just June.

By five, the pub’s got its own regulars, a different crowd than the diner’s but the same instinct. A group’s tucked into the corner booth playing cribbage, matchsticks standing in for pennies, and nobody’s kept score on paper in years because nobody needs to. A guy’s setting up in the other corner with a guitar and a small amp, not for a crowd, just because the evening needs a soundtrack and he’s willing to be it for the price of a few pints. Two tables over, somebody’s arguing that the new school bus company can’t find a road they haven’t been late to yet, and somebody else is defending them like they’re kin, and neither one is actually trying to win, they’re just enjoying having something to be wrong about together. The kitchen’s sending out Guinness beef stew like it’s the only thing on the menu, which by 7:30 it basically is, and nobody in here is asking for the wine list, because we all know there isn’t one.

None of this is for anyone. Nobody’s even tracking the cribbage game. Nobody’s going to post a review of the Guinness Stew (well, I might, it’s fabulous by way). It’s just Tuesday, being exactly what Tuesday is, in a town with enough of the right things that Tuesday is worth getting out of the house for.

Here’s to knowing which kind of town you want to wake up to in March, and which one you want to walk into on a Tuesday night.

🧭 Jenn

Keys to the Lakes

Our last installment in this history series one ended with a line I haven’t stopped thinking about: competing claims on land that had never been understood as ownable in the first place. That’s where I want to start, except this time I’m not looking at the people. I’m looking at the paper.

I spend a fair amount of my working life inside chains of title. Part of the job of representing my clients well is making sure that when they sign on the dotted line, the title to what they’re purchasing is clear. Somebody wants to know how a piece of land got from there to here, who held it before them, whether anything upstream might come back to bite them. Most of the time the chain goes back sixty, eighty years and the story is boring in the way land records are supposed to be boring. And sometimes, folks are just curious about the history of their new home. Once in a while I get curious enough myself to keep pulling the thread past what’s useful for a transaction, just to see where it goes. And as I’ve been digging into the history of the region overall, I wanted to see where the first official thread in the tapestry started. That’s what this piece is, the first thread, which is pretty frayed as it turns out.

Our story starts back in 1629.

That year, three documents were produced that, between them, invented this place I now call home on paper. Two came from a room in England. One is supposed to have originated here, but probably didn’t.

Let’s start with the one that claims to be local. On May 17, 1629, four Pennacook sagamores, Passaconaway, Runaawit, Rowes, and Wehanownowit, reportedly deeded a swath of land between the Merrimack and Piscataqua rivers, roughly thirty miles by thirty, to a handful of Englishmen including a minister named John Wheelwright. In exchange, Passaconaway was to receive one coat of trucking cloth a year, and his people kept the right to fish, fowl, hunt, and plant on the land they’d just supposedly signed away. It reads, on its face, like an unusually respectful and mutually beneficial transaction for its era.

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Here’s the problem. Nobody saw this deed until 1707, discovered in a file in a Maine registry, seventy-eight years after it was dated and twenty-eight years after Wheelwright died, in the middle of a lawsuit over land it happened to cover. Wheelwright himself didn’t even arrive in New England until 1637, eight years after he supposedly executed it. Historians have been arguing about it since the 1820s. The current scholarly consensus, as far as I can find it, leans toward forgery. Not a shady side deal. An invention, out of whole cloth as my grandma used to say, assembled decades later to backfill a signature nobody had actually gotten.

But let’s imagine for a minute it had been real. Say Passaconaway sat down and put his mark on exactly that document, freely, in full possession of his considerable diplomatic sense, which piece one already made clear was formidable. Would it have meant what the English needed it to mean?

I don’t think that’s a rhetorical question with an easy answer, and I want to be careful here, because it’s not about anyone being fooled. Abenaki land relations, as best as the scholarship lays them out, were built around territory and use, who had the right to hunt, fish, plant, and move through a given stretch of ground, often shared across bands and seasons, tied to kinship and reciprocal obligation. It was a complex system. What doesn’t seem to have entered into that complex system is the specific idea the English were operating under: land as a fixed, exclusive, permanently transferable asset, the kind of thing one party could hand to another forever and then no longer have any claim to at all. Even the terms of the disputed deed hint at this mismatch. Reserved fishing and hunting rights, an annual coat of cloth. That’s not the language of a sale. That’s the language of an ongoing relationship, which is closer to how territory seems to have actually worked here before contact. If the two sides had genuinely sat down together, they might both have walked away certain they’d understood each other, and still have been describing two different transactions.

Now the other two documents, made in England, by Englishmen, about land none of them had ever walked.

On November 7, 1629, the Council for New England granted Captain John Mason a tract between the Merrimack and Piscataqua rivers and called it, for the first time on paper, New Hampshire. Ten days later, on November 17, Mason and his partners secured a second grant just to the west, for a region they named Laconia, from the Latin for lake country. They believed it bordered Lake Champlain. It didn’t. Mason had gotten the Piscataqua’s headwaters wrong by roughly a hundred miles. He named a lake region for lakes he’d misplaced on a map representing land he’d never stood on.

I want to sit with that for a second, because it’s the detail that got me. The name that eventually becomes Laconia, the actual town, the actual region I live in, the words on my own listing sheets, originated in a clerical error made by a man in London who thought this place bordered different water entirely. Land can be surveyed wrong. A boundary can be off by a chain or two. But this was invented sight unseen, on the strength of a guess, and the guess stuck.

Between them, those two documents cover the same eighteen days in November 1629. Neither one involves anyone who was actually here. And the one document from that same year that does claim to involve the people who were here is the one nobody can vouch for.

Fast forward. Mason’s grant passed down through his family for a century, getting less useful and more disputed with every generation, until 1746, when a descendant six times removed, John Tufton Mason, sold the whole claim to twelve Portsmouth investors for fifteen hundred pounds. They called themselves the Masonian Proprietors. It’s their patent that eventually produces the actual town charters across the interior of New Hampshire, this region included, starting in the 1750s and 60s.

Wolfeboro’s charter is dated October 5, 1759, signed by Governor Benning Wentworth, naming the town for a general who’d died that same year at Quebec. Read the charter language and you get the standard formula of the period: land divided into shares among a small group of Portsmouth men, most of whom never set foot here, the crown reserving every white pine tree of a certain size for the Royal Navy’s masts, a nominal yearly rent of one ear of corn if demanded, later replaced by a shilling per hundred acres, payable each December at the council chamber back in Portsmouth. The town existed on paper for nine years before it existed as a town. First settlement wasn’t until 1768. Incorporation came in 1770. By the time any of that happened, sustained Abenaki presence in this immediate area had already thinned considerably, a slower unraveling that piece one already walked through in more depth than I want to repeat here.

I wonder what my clients would say if I told them their five acres, likely valued today somewhere in the $500-$700K range if there’s a livable house on it, was once worth a few kernels of corn.

Here’s where the work I actually do bumps into this. Real estate has a formal name for the problem I raised earlier about Passaconaway and Wheelwright. It’s called a meeting of the minds. A contract, including a deed, isn’t valid just because two parties signed it. Both parties have to be agreeing to the same thing, understanding the transaction in the same terms. That’s not a capacity question. It’s not about who was sophisticated enough to negotiate, because everything about Passaconaway’s documented diplomacy argues against that reading. It’s a translation question. If one side is agreeing to shared, ongoing, seasonal use and the other side believes it’s receiving permanent, exclusive ownership forever, they can both sign in good faith and still not have made the same deal. Modern property law spends a lot of effort making sure that gap can’t happen, precisely because land is wealth and wealth transfers this size don’t get undone. There was nothing here doing that work in 1629, and I’d guess the ambiguity suited exactly one side of the table, if there ever was a table and document in 1629 at all.

What I keep coming back to isn’t any single document. It’s the shape of the whole chain. Council grant to Mason. Mason to his descendants. Descendants to the Masonian Proprietors. Proprietors to Wentworth’s charters. Charters to the actual parcels that, a few sales later, become the addresses I pull up on a Thursday afternoon to made a recommendation for what we should list at in this current shifting market. At no point in a hundred and thirty years does a real, verifiable signature from anyone who already lived here appear in that chain. The only attempt to include one is the one that scholarship now doubts existed at all, and even if it had existed, I’m not convinced it would have settled anything. And somehow, it doesn’t matter. Because at some point each lot did get a title that some clerk somewhere decided was clean, and now we can trace it from sale to sale in a way that protects my clients.

The land itself, of course, never asked to be named, granted, or misplaced on a map. It has just kept being beautiful lake country, long before and long after the paperwork existed.

If this made you think of someone who’d want to read it, send it their way.

Here's to reading the fine print, even when it's three hundred years old.

🧭 Jenn

Keys to the Lakes

Here’s the thing not all fairgoers will admit. Not every fall event with a Ferris wheel is a fair. A fair, a real one, comes out of an agricultural society. It has a livestock building where someone’s kid has been getting up at five in the morning all summer to prep a rabbit for judging, and a judge who genuinely does not care whose kid it is. It has a pulling ring where the crowd goes quiet and then roars. It has jam and honey and pickles lined up in mason jars with handwritten cards, competing for a ribbon that means something to exactly the people standing in that building and nobody else, which is precisely why it matters.

My cousins in Ohio actually lived that version. Rabbits, goats, the whole 4-H circuit, showing animals they’d raised themselves. I was the city kid who visited in the summer and thought the whole operation was slightly magical but always had to go home for the start of school before the actual fair happened. But if I’m honest about where the real obsession comes from, it’s less based in real life than that. It’s sick days home from school, flipping channels to AMC, watching Rodgers and Hammerstein’s State Fair for the tenth time. I will still, given the right stretch of fair traffic, break into “It’s a Grand Night for Singing” purely to torture my teenagers, who have made it extremely clear this is not appreciated.

A harvest festival gives you a hayride and a craft table. A fair gives you a hundred years of a farming county’s pride, wrapped around a midway,sprinkled with experimental cuisine and the same snacks that have people pleasers forever. Once you’ve felt the difference, you can’t unfeel it.

I’ve been going to our regional fairs for about 20 years now, and I’ve been paying closer attention to the New Hampshire and Maine ones since I landed near Lovell Lake. Here’s where I’d actually spend a Saturday, what each one is actually like once you’re standing in it, and who each one is for.

Topsfield Fair — The One That Started It For Me

Topsfield is the fair I know best, and it’s not even in this state. It’s over the Massachusetts line, on the North Shore-ish, and it’s the oldest county fair in the country, which you can feel the second you’re through the gate. Not because it feels particularly old. Because it feels like it’s been getting this right for two centuries and has no plans to stop.

It’s chaos, and I mean that as a compliment. The crowd is thick enough that you stop trying to walk in a straight line and just let the current take you. Fried food smell hits you before you’ve paid for parking. I have a strict no fried food rule for myself, most days of the year, except at a fair, where the rule simply does not apply. Something on a stick is non negotiable. I don’t ask what it is anymore, I just get in the longest line and trust my fellow fairgoers.

But the part that gets me every time isn’t the midway. It’s the exhibition halls. Rows of quilts, jars of jam with a ribbon or without one, a woman explaining to a stranger exactly how she got her chutney that color. I go in for the rides and I leave thinking about pigs I don’t have the skills to care for (yet!). If you’ve ever wondered where my interest in homesteading actually started, it’s booths like these. Years of walking past them clearly did something.

This one is for anyone who wants the full sensory overload version of a fair. Big crowds, real chaos, and worth every minute of the parking wait.

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Deerfield Fair — New Hampshire’s Own

Deerfield is what people mean when they picture a New Hampshire fair in their head, and it earns that reputation honestly. It’s the oldest agricultural fair in the state, it runs the first weekend of October when the foliage is doing its best work, and the fairgrounds are old enough to be genuinely historic rather than dressed up to look that way.

What makes Deerfield different from the bigger fairs is scale. You can actually cover it in a day without feeling like you missed half the fair. The livestock shows are serious, the ox pulling draws a real crowd that gets loud in a way that surprises first timers, and the food, apple crisp, maple bacon fried dough, cider donuts made right there, is the kind of thing you plan your walking route around. Don’t miss the sheep shearing, its a whole thing in and of itself. If you want one fair that captures what makes this whole tradition worth defending, and you don’t want to commit an entire week to it, this is the one.

Go early in the run if you can. Thursday and Friday crowds are a different experience than Saturday, when the whole state, and half of Massachusetts, seems to show up at once.

Sandwich Fair — The One In My Backyard

Sandwich is close enough to home that it doesn’t feel like an event I plan for so much as one that someone pings me a text about one afternoon and we just go. It’s smaller than Deerfield, smaller than Fryeburg by a wide margin, and that’s the whole appeal. It sits at the foothills of the White Mountains, it happens over Columbus Day weekend, and it still runs like a town fair even though everyone in three counties knows about it.

There’s a parade through the middle of it, an antique auto procession one day and a proper street parade the next, and the fairgrounds themselves are unpretentious in a way that feels just right for this part of the state. Cattle sheds, oxen barns, a skillet toss competition that draws more genuine enthusiasm than makes sense and always makes me think of that song from Chicago, “He Had It Coming.” In any case, Sandwich is a fair that hasn’t tried to become anything bigger than what it already is, and I respect that.

This is the one for someone who wants the real thing without the crowd math of a major fair. Bring layers. Once the sun starts going down in that valley, the temperature drops fast.

Fryeburg Fair — Know What You’re Signing Up For

Fryeburg is Maine’s answer to all of this, and it is not a smaller version of anything. It runs for eight full days, right around the state line, close enough to the Lakes Region that plenty of my neighbors treat it as a local tradition rather than a road trip. The scale is genuinely different from every fair I’ve named so far. Livestock shows that run all week, the largest ox and steer competition of its kind anywhere, and a midway that takes real effort to see in a single visit.

People camp out across from the fairgrounds for the whole run, which tells you something about the commitment level of a true Fryeburg regular. This isn’t a fair you casually pop into for an afternoon. It’s basically the Disney World of fairs, second in my personal experience only to the Minnesota State Fair, which is unique in its awesomeness. Go in with a plan, or go in accepting you’ll only see a fraction of it and that’s fine too. Weekday visits are dramatically calmer than the closing weekend, which draws the kind of crowd that turns the whole town of Fryeburg into one ginormous parking lot.

How To Actually Do This

Here’s what I’ve learned after enough Octobers of this. You cannot do it all, at any single fair, in a single visit. There is always another barn, another ring, another vendor row you didn’t get to. The trick isn’t trying to see everything. It’s looking at the schedule ahead of time and deciding what’s not for you this year, so you’re not standing in the middle of a field at 3pm trying to make that decision on the fly. I recently found a note in my phone’s app that I made to myself at the 2024 Fryeburg Fair. It read: “next year, come early. see sheep, maybe buy? eat churros first no kamikaze.” So I guess that’s what I’ll do this year.

If you’re going to any of the fairs, plan to sit in traffic. Genuinely, budget for it. It’s not a flaw in the day, it’s just part of the day, and honestly, a captive audience for showtunes. And, check the weather but like a true New Englander, know that it’s never bad, it just requires different clothes.

If this made you think of the person in your life who’d fight for a caramel apple, send it their way.

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🧭 Jenn

Keys to the Lakes

Here’s the biggest piece I think gets skipped, though, when people complain about how “crowded” with “summer people” our towns are now. Most rural places in this country are shrinking. Young people leave for work, the school enrollment drops until someone has to have the conversation about closing it, the general store holds on for a decade past when it should have folded and then finally joins a string of empty storefronts on what used to be vibrant main streets. That is the ordinary fate of a small, rural place in America right now. That’s not what we’re experiencing. New Hampshire has had more deaths than births, statewide, every single year since 2017. Whatever growth this state has, all of it, comes from people choosing to move here. And up here specifically, that choosing isn’t going to stop, probably ever. It’s slowed some since the pandemic years, the way anything returns to the mean after a big leap, but towns like Brookfield, Tuftonboro, and Moultonborough are still growing at more than double the state’s overall rate. Not every rural region gets to have this “problem.” I try to remind my neighbors of that sometimes, even though it also reminds them that I called Boston home for 15 years before moving here not too long ago — at least not too long ago as the locals count belonging.

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For a long time the shorthand for who was moving in was easy, and mostly accurate. Massachusetts retirees. Connecticut families with a camp that finally became the only house. People who summered here as kids and made it permanent once the grandchildren showed up. That story hasn’t disappeared, but it’s stopped being the whole story. Statewide, adults in their twenties and thirties and early forties, the exact years people are building a career and starting a family, now account for more than half of New Hampshire’s net growth from other states. Not retirees. Not weekenders. People trying to build an actual working life somewhere with a hybrid schedule in one hand and a school enrollment number in the other. When people tell me why they are coming to this region, the honest answer is rarely about money. It’s family, more often than not; somebody’s parents, somebody’s siblings, a version of New England they didn’t want to leave behind entirely. New Hampshire’s tax picture helps too, obviously; no tax on wages, and as of last year, none on interest and dividends either, which matters more to someone living off investments than to a family living off a paycheck. Climate comes up more than it used to as well, New England increasingly framed as a place with less exposure to the kind of heat and water reshaping the Gulf Coast and the Southwest.

Now the part I actually want to say plainly, because it is a conundrum that is absolutely solvable if we talk about it collectively with an aim of understanding that some situations aren’t either/or problems, they are yes/and problems. The same qualities that make this place so attractive to so many are making it harder for the people who already live here to stay in a way that will continue to work for them for another generation. A median single-family home in New Hampshire crossed half a million dollars last year, up nearly eighty percent since 2019. To buy that home without being what the economists call cost-burdened, a household needs to earn around a hundred fifty-eight thousand dollars a year. Roughly three in ten New Hampshire households clear that. I think about the people I know, some of them older, some of them just starting out, whose plan was always to move up eventually; into something bigger once the family grew, something newer and easier to heat once the stairs got harder. That move-up market is the one that’s disappeared out from under a lot of people. Their current home is worth more on paper than it’s ever been, and that number does them almost no good, because everything they’d move into costs more than the equity covers. They’re not being pushed out exactly. They’re stuck in place, which is its own kind of squeeze, quieter and less talked about than the one that gets all the headlines.

It would be easy to make this a story about newcomers, and I don’t think that’s an honest, or the most interesting, one. This region never had much housing inventory to begin with. Steep land, protected shoreline, small town centers that were never built to expand much past their original footprint. Add real demand of any kind, retiree or young family or someone working three remote days a week out of a rented camp, to a supply that was already tight, and prices move the way they’ve moved regardless of exactly who’s doing the buying. It isn’t locals against newcomers. It’s a small, slow-growing, genuinely beautiful place meeting more interest than it has room to hold gracefully, the way it’s been meeting that interest, on and off, since it became a summer resort back in 1838 or whatever. We’re just meeting more of it than usual, from a wider range of people, at a moment when there’s less room to spare than there used to be.

I don’t have a tidy answer for what to do about any of it, and I’d be suspicious of anyone who claims to. What I keep landing on is that this has always been a place people choose. The question that actually interests me isn’t whether people will keep coming. They will; the numbers say so, and so does every October sunset that makes someone in a rental car pull over on 109 to take a picture.

The real question is what it takes for the people who are already here, who’ve shoveled the same driveway for forty winters running, to still have a place in whatever comes next. I’d really love to hear what you think about this, whether you’ve lived here from the day you were born or the signature on your new place is still wet.

Here’s to figuring it out together, because we all deserve this place, and each other.

🧭 Jenn

Keys to the Lakes

Here is what the beginning of the end of summer feels like, and I know because it happened to me this morning.

I met a friend for coffee at North Main Cafe (try the Almond Cake), on Main Street in Wolfeboro, and I parked right in front. Not near the front. In front. Then I drove two blocks to my office and parked right in front of that too, which in July would have taken me fifteen minutes and a breathing exercise I learned in therapy. I didn’t think much of it today; I just found a spot twice in one morning without circling once.

That’s the tell. Not a quiet street. Not an empty beach. A woman getting two parking spots on Main Street before ten a.m., the week of Labor Day, and feeling almost smug about it.

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That’s how I know this is home now, even though I haven’t hit the two decade mark that seems to count with those who grew up here. Not because anyone said something so much as because I felt it. I clocked the season turning on Main Street before anyone told me it had, the way you know a friend’s mood has shifted before they’ve said a word. Nobody posted about it. Nobody sent a text announcing the tourists were thinning out. I just parked twice without trying and knew this is it.

The parking monitor hasn’t caught up yet, which is its own kind of proof. He is still out there chalking tires in yellow, still working the two-hour rule with the same love for rules he brought to it the week of July 4th, when there wasn’t a spot to be had for love or money. So for one more week I will begrudgingly go move my car at the appropriate interval, for a rule that no longer needs enforcing, because the street has emptied out faster than the systems built to manage it. That gap, the lag between a place quieting down and the place noticing it’s quieted down, might be the truest image I have for this whole stretch of September.

Because the visitors haven’t left. They’ve retreated to the weekend, which is a different thing entirely, and worth being honest about. If you come through Wolfeboro on a Saturday in the next eight weeks, you will still wait for a table. You will still see the Mount Washington pull out with a full load and sound her horn like she means it, same as she did on the Fourth. The lake will still be doing its lake things on both sides of the parking question, Winnipeesaukee crowded and busy, Wentworth and Lovell keeping to themselves the way they always have. Weekends, for now, still belong partly to somebody else.

But Monday through Friday. Those are mostly ours again.

That’s the part I didn’t expect to feel as sharply as I do. It’s not that the season ends. It’s that I get five out of seven days of it back, and the two I don’t get back are the two I was least attached to anyway. I don’t need Saturday morning at Lino’s to have space at the counter. I need Thursday morning to be mine, and this week, for the first time since May, it will be.

I was standing on my back stairs this morning, watching the dogs wrestle in the wet grass, when the knitting circle text came through. Seven words: My house, Thursday, bring your current project. Not an invitation, as assumption that we all know what that all means. I stood there a second longer than the text warranted, picturing the women I haven’t seen except in passing for the last three months, circled around the kitchen table by the window, a dog under somebody’s chair, the particular buzz and contentment of a room where everyone’s hands are busy and nobody has to perform being interesting. I didn’t carefully compose a text back. I gave it a thumbs up and watched 6 others roll in. More importantly, I felt my shoulders drop about an inch, which is apparently what late August has been costing me without my noticing.

Keys’s Substack

The Honest Summer

When we moved up here, it was in part to fulfill a long-held homesteading fantasy. One of the first instantiations of that dream, other than the land and the old farmhouse, was the addition of two young Great Pyrenees. These dogs have been bred for generations to guard something, to make independent decisions, and to roam while doing these things. I got…

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3 months ago · Keys to the Lakes

I want to resist the tidy version of this, the one where the town exhales and goes still and even though we all love summer here so much, we all rejoice in the emptier streets and quieter lakes. That’s not what’s happening. What’s happening is more complex and, I think, more honest: the retiree down the road hasn’t felt any of this at all, because her days were never on the visitor’s clock to begin with, and she’ll tell you as much if you ask, mildly amused that the rest of us are only now catching up to a rhythm she just always lives in. The visitor’s week has shrunk from seven days to two. And my week, the year-rounder week, the one built around driving to showings and back and squeezing errands into the gaps, that week just got more expansive and generous and quieter all at once.

So no, I won’t tell you it’s gone quiet, because for the next eight weeks it will still be loud again on a Saturday and I’ll be back to circling for that same spot in front of North Main. And anyway, life here in the fall and winter is so rich and varied and busy in a different way than summer. What I’ll tell you instead is smaller and more specific. This morning I parked twice on Main Street without trying, and for one more week, I still have to go move my car from one spot to another. By next Tuesday, I won’t have to. That’s the whole shift, right there. Not an ending. A door opening five days at a time, the season still holding onto weekends for now.

🧭 Jenn

Keys to the Lakes

The weekdays are the tell. Today I found a parking spot more quickly than I have since May. The kid who’s been scooping ice cream all summer told me his last day is next Tuesday. He wants a few days of true vacation before he’s back at practices and in classrooms. But come Friday, the docks fill again, the parking lots along 16 and main streets in towns all over are worse than they ever were in peak season (because leaves, people). September isn’t the season ending. It’s the season getting particular about which days it shows up for.

In the meantime, there is, it turns out, an enormous amount happening. Concerts and craft fairs and a five-hour boxing fundraiser and a faire for pagans and a parade made entirely of lantern light on a lake that used to be a farm. Here’s a selection from the month. As always, let me know what I’ve missed that I should know about by leaving a comment!

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Old Home Days & Town Celebrations

Meredith Old Home Day, Main Street, Meredith. Saturday, September 19, 10 a.m. to 3 p.m. Second year back after a seventy-year gap, leaning into the theme “Honoring Yesterday, Celebrating Today.” Parade at 10, live music at the Calvary Bible Church lot, a dunk tank, an egg toss, a pie eating contest I will be watching and not entering.

Wolfeboro Fall Festival, 50 Martin Hill Road, Wolfeboro. Saturday, September 26, 9 a.m.

Lantern Light & the Lake

Lantern-Making Workshop, Cook Memorial Library, Tamworth. Tuesday, September 1, 3 to 5 p.m. Free, hosted by the Arts Council of Tamworth and the Chocorua Lake Conservancy, building lanterns ahead of the parade below.

Chocorua Lake Conservancy Annual Picnic & Parade of Lights, Chocorua Lake, Tamworth. Sunday, September 6, picnic at 6 p.m., lantern parade on the water at dusk. Bring your own picnic, a chair, and a headlamp for the walk back. This is the kind of event that makes you understand why people who’ve never lived here still talk about this lake.

Lakes Region Lantern Festival, Center Harbor. Sunday, September 6, 4:30 p.m., lantern launch at dusk, around 7:30 p.m. Inaugural year for this one, hosted by the Lakes Region Tourism Association with the M/S Mount Washington docked for the evening, food and drink aboard. Food trucks, live music, a bouncy house for the kids, and then hundreds of lanterns going up over Winnipesaukee as the light finally gives out. Lanterns can be purchased and personalized ahead of time at lakesregionlanternfestival.org, worth doing if you want to send one up for someone in particular.

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Stage, Gallery & Story

Collected Stories, The Barnstormers Theatre, Tamworth. September 4 (7:30 p.m.), September 5 (2 p.m. and 7:30 p.m.), September 6 (5 p.m.). Donald Margulies’ play about an established author, her protégé, and the line between mentorship and theft.

“The Wonder of the Woods, Waters & Whites,” the lakes gallery at chi-lin, 135 Eastman Road, Laconia. Through September 23, Wednesday through Saturday, 11 a.m. to 5 p.m. A landscape exhibit at a gallery that’s been showing contemporary New England and Asian art since 1981.

Creative Writing at the 1820 Clark Barn, Clark House Museum Complex, Wolfeboro. Wednesday, September 23, 3 p.m.

History & Lectures

Meredith Historical Society Annual Open House, Main Street Museum, 45 Main St., Meredith. Tuesday, September 1, 5 to 7 p.m. Free hot dogs, chips, and volunteers happy to talk Meredith history.

“Brewing in New Hampshire,” In the Barn at Clark Museum, Wolfeboro. Monday, September 7, 7 to 9 p.m. Author Glen Knoblock, hosted by the Wolfeboro Historical Society. Free.

Wright Museum of WWII Lecture Series, Wolfeboro. Tuesdays through September 29. Check wrightmuseum.org for the week’s topic.

Music at Bank NH Pavilion, Gilford

A genuinely stacked month. Parker McCollum, Friday the 4th, 7:30 p.m. ZZ Top with George Thorogood & The Destroyers, Saturday the 5th, 7 p.m. Tedeschi Trucks Band with Lukas Nelson, Sunday the 6th, 7 p.m. O.A.R. with Gavin DeGraw and KT Tunstall, Sunday the 13th, 6:30 p.m. Dan + Shay with Tyler Hubbard and Josh Ross, Friday the 18th, 7:30 p.m. And Jason Aldean closes it out with two nights, Friday the 25th and Saturday the 26th, both 7:30 p.m., with Chase Matthew, Mackenzie Carpenter, and Dee Jay Silver.

Fundraisers & Community Good

Gala en Blanc, Castle in the Clouds, Moultonborough. Friday, September 4, 5 to 10:30 p.m. The Castle’s white-attire fundraiser, doubling this year as the 20th anniversary of the Castle Preservation Society.

Wolfeboro Lions Club 21st Annual Golf Tournament, Indian Mound Golf Course, Ossipee. Tuesday, September 8, 7:30 a.m.

Rock Steady Boxing Lakes Region 8th Annual 5K Run/Walk, The Downtown Gym, 171 Fair Street, Laconia. Saturday, September 19, 9 a.m. Raises funds for the Adopt-A-Boxer program, which uses boxing training to help people with Parkinson’s.

“Your Health Is Wealth” Autumn Wellness Symposium & Luncheon, Birch Hill Farm, Gilford. Tuesday, September 22, 11 a.m. to 1 p.m. Mid-State Health Center and Bank of New Hampshire on nutrition, healthcare, and financial planning, proceeds to Mid-State’s food security program.

Be A Hero 5K Run/Walk, Castle in the Clouds, Moultonborough. Saturday, September 26. Now in its fifth year, benefiting the NH Humane Society, dogs welcome on leash, costumes encouraged.

Veterans Count Lakes Region Red, White and Brew, Funspot, Laconia. Saturday, September 26, 12 to 4 p.m. 10th annual, craft beer, car show, and live music from the Bob Pratte Band, benefiting NH service members and veterans’ families.

On the Water & Wheels

Discover Squam Guided Lake Cruise, Squam Lakes Natural Science Center, Holderness. Daily, 1 to 2:30 p.m., through October 12. Ninety minutes on a canopied pontoon boat past the loons and eagles, on the lake where On Golden Pond was filmed.

Laconia Biketemberfest Fall Rally, Big House, Weirs Beach, Laconia. Friday through Sunday, September 11-13.

Ice Cream Tamwich, Tamworth. Sunday, September 13. A new gravel ride through the back roads, finishing with ice cream.

Crawford Ridgepole Trail Workday, Burleigh Farm Road, Holderness. Sunday, September 20, 9 a.m. to 3 p.m. Squam Lakes Association’s Lakes Region Conservation Corps leads volunteers clearing trail ahead of the Squam Ridge Race. First-timers welcome, tools provided.

Markets, Makers & Weekly Rituals

Fiber Arts Group, Belknap Mill, Laconia. Tuesdays, 10 a.m. to noon. Bring your own knitting, spinning, or embroidery.

Classic Car Cruise Night, Tilt’n Diner, Tilton. Thursdays, 5 to 7 p.m. Held in memory of longtime organizer Walter Krauz, Jr.

Wicked Wednesdays, Silver Sage Cottage, Tilton. Second Wednesday of the month, September 9, 5 to 7 p.m. A low-key community gathering the shop itself describes as “a porch light for the weird and wonderful.”

Mill After Hours: Sock Hop, Belknap Mill & Rotary Park, Laconia. Friday, September 11, 5 to 8 p.m. Classic cars, live music from the Rockin’ Daddios, a gallery opening, and an outdoor screening of Grease. Costumes and root beer floats encouraged.

Fairs & Festivals

Labor Day Weekend Craft Fair, Gunstock Mountain Resort, Gilford. Saturday and Sunday, September 5-6, 10 a.m. to 5 p.m. Over 100 exhibitors, free admission, leashed pets welcome.

5th Annual New Hampshire Pagans Faire, Belknap County Fairground, Belmont. Friday evening September 18, Faire days September 19-20. Local artisans and community resources, open to any path, described by organizers as rooted in kindness and inclusivity.

Lagerfest, Vulgar Brewing Company, Franklin. Saturday, September 19, noon to 4 p.m. Breweries from across New England pouring nothing but lager, plus a running game of Rock, Paper, Scissors.

Nightlife

Wolfeboro Inn Dinner Show: Frank Santos Jr., The Wolfeboro Inn, Wolfeboro. Sunday, September 13, 6 p.m. Comedy hypnosis and dinner, 18+.

Anytime in September

Apple picking opens up early to mid-month at Surowiec Farm in Sanbornton and at Stone Mountain Farm and Smith Orchard in Belmont. The Squam Lakes Natural Science Center’s Live Animal Exhibit Trail stays open daily through November 1. And the lake, if you catch it in that late gold hour before the light goes, is still warm enough to make you forget the calendar entirely, at least until you’re standing on the dock afterward, a little cold, watching the color drain back out of the water the way it does every night this time of year, a little earlier than the night before.

Here's to the lasts of the season. Last cone. Last swim. Last sunset after seven. Enjoy them while they last.

🧭 Jenn
Keys to the Lakes

I’m forty-seven. I’m definitely not retired. My kids are mostly self-sufficient, I’m still fairly new to this area, and I like trying new things, and it turns out that’s plenty of reason to call this my own third chapter even without a gold watch involved. A little over a year ago I joined the Lakes Region Newcomers Club, mostly because I wanted to meet people and didn’t have a better plan than that. I was a little worried that because I had already lived here for a year, and been vacationing here for 15, I might not fit the criteria. Turns out, I needed have worried. There are members in the group who first joined twenty years ago…but its just that much fun.

The club itself is a large, well-organized thing. There’s a governance committee and bylaws, which sounds almost comically formal for an organization whose real function is helping people not eat lunch alone, but the structure is what lets each group underneath it run itself differently without the whole thing falling apart. Some groups are outdoorsy, some are social, some exist entirely around a shared, specific interest. What they have in common is that nobody’s checking whether you showed up last time, they’re just checking that you’re making a connection.

I just agreed to co-lead the Creative Writing group for the next year or so, which meets once a month, usually at a coffee shop or in a room at the Wolfeboro library. Someone in the group picks a theme, everyone writes a piece to it over the following weeks, and then we read our pages aloud and offer feedback using roses, thorns, and buds, what worked, what didn’t, and what has potential if it’s pushed further. Some of the members are published writers. Most of us are just imaginative neighbors who wanted somewhere to put the sentences. We’re adding poetry open mic nights at local restaurants this winter, which feels like the group stretching in new ways.

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I’m also a fair regular at Lunch Bunch, which is exactly what it sounds like, a different restaurant somewhere in the region every month, everyone orders and pays for their own meal, and the whole appeal is that you never know who’s going to end up across the table from you. I’ve dipped into the knitting group too, which meets a couple of times a month at various members’ homes, welcomes total beginners next to genuine experts, and is where I learned that I’m what’s called a process knitter. I love the feel of it, the calm of knit and purl, and I have never finished a single project. Not one. The group didn’t seem to think that was strange, though they did offer to help me out if I ever decide I need to cast off instead of just casting on. Apparently a lot of knitting is just knitting. And a lot of people are really just welcoming.

Here’s the thing nobody tells you going in: some members join one group and that’s their whole social world, and that’s enough for them. I turned out to be a dabbler. I flit between groups, show up to some events more than others, and the connections vary in depth accordingly. But a few of the women from Creative Writing have become people I genuinely can’t imagine not knowing now. We started going to trivia together outside of the writing group entirely, and somewhere along the way we pulled in a friend one of us made through the mindful movement group, and another who came from the wine SIG. The newcomers club didn’t introduce us to each other directly so much as it kept putting us in rooms until we did the rest ourselves.

That’s really the point, and it took me a while to see it clearly. It isn’t about finishing the sweater or making every meeting or racking up some tally of groups joined. It’s about putting yourself in front of other people who have also chosen this place, on purpose, at whatever stage of life brought them here, and letting some of those encounters turn into something that outlasts the original reason you showed up.

If you’re weighing a move here and wondering whether you’d actually find your people, whatever chapter you’d be arriving in, this is some of what that can look like from the inside. Not automatic, not instant, but real, and it’s there if you’re willing to show up more than once.

And if you would like to come share a poem or grab lunch, let me know; I would love to introduce you to 250 of my nearest and dearest neighbors.

🧭 Jenn, Keys to the Lakes

This is part of an ongoing series about what the third chapter of life actually looks like in the Lakes Region, for the people who chose it.

Most people driving through don’t stop. Most people who’ve heard of this region at all have heard of Winnipesaukee, or Wolfeboro, or North Conway if they lean more snow than water. Tamworth isn’t on that list, and I kind of really love that about it.

Here’s the thing about a town in the middle. Everyone assumes it’s a compromise, the place you settle for when you can’t have the lake and can’t have the mountains either. It’s not. It’s the answer to a question most people don’t know to ask: do you actually have to choose between the two, or do you just think you have to?

The feel of the place

Tamworth is small on paper, about 2,800 people spread across five villages: Tamworth Village itself, Chocorua, South Tamworth, Wonalancet, and Whittier. But it doesn’t read as a satellite of anywhere. It’s not a quieter Winnipesaukee lake town and it’s not a budget North Conway. It has its own multiverse with at least three different centers of gravity: working farms and growers, artists and theater people, and people who love the great outdoors, whether part of the year or always. And one of the coolest parts is that these groups all coexist in a way that mostly works because everyone love the place wholeheartedly. Nobody moves to Tamworth by accident.

The theater is the tell

Let’s start with the Barnstormers. It’s easy to drive through Tamworth Village, see the white church and the little brick library and assume you’re looking at a postcard with no substance behind it. Or the well-preserved memory of how life used to be. Then you find out the theater on Main Street has been running since 1931, that it’s the oldest continuously operating professional summer theatre in the country, and that it was founded by Grover Cleveland’s son in a converted general store. Eight shows, eight consecutive weeks, every summer, one of only three Equity houses in the entire state. That’s not a hobby or someone’s vanity project. That’s a town that decided, almost a century ago, that culture wasn’t something they wanted to have to drive to Boston for. And then they’ve decided, year after year, to fund it, support it, and enjoy it.

I bring this up first because it tells you what kind of place this actually is. Not “cute.” Not “quaint,” a word I try to avoid because it usually means some city person can’t imagine living there (mea culpa — used to use this word to describe coastal Maine all the time, my bad.) The Arts Council runs a live painting competition every spring where artists work in different media on the same subject in real time. It’s a wonder to watch, whether you have any artistic talent yourself or not. The Remick farm has been worked for over two hundred years and will let you wander pastures with grazing cows, then walk you through a doctor’s office frozen at 1935. The distillery on the edge of the village makes gin from foraged pine resin and a whiskey aged with venison in it, which sounds like a bit until you taste it and realize they’re not joking around. This is a town with two libraries for 2,800 people. That ratio tells you something.

The honest part

Tamworth is not a lake town in the way that countless other towns around here are. Chocorua Lake is small, stunning, and mostly conserved land with no motors allowed, which gets you the single best reflection of a mountain you’ll find in this state and almost no boat traffic to go with it. White Lake State Park gives you public swimming and camping, which is lovely and also not the same as owning a dock. If your version of lake life involves a boat lift and a slip with your name on it, you want Winnipesaukee or one of the approximately 20 other lakes where people boat in the region.

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There’s a broader honesty worth naming too. This is a lifestyle town, not a convenience town, and that cuts both ways. You’ll drive for most errands, for a wider entertainment selection, for specialty retail, for anything beyond urgent care. Realistically, you’ll have to drive for groceries unless you are very intentional about eating locally and seasonally…and know how to can vegetables. Expect wells and septic instead of town water and sewer on a lot of properties, dirt roads that need real winter maintenance, and internet that should be evaluated as part of your due diligence the same way roofs and chimneys are. None of that is a flaw exactly. It’s just what “unpolished” actually means. Older homes here tend to be full of character and full of questions, so evaluating systems, age, and access matters more than it would in a subdivision with a homeowners’ association telling everyone what color to paint the shutters.

What you get in return is proximity without the premium and a beauty and pace of life that cannot be measured in property values. Conway is about twenty five minutes away for groceries, hardware, and the hospital. Wolfeboro, with its marinas and its lake-town crowds, is roughly thirty-five minutes the other direction. That’s what makes Tamworth a real sweet spot: most towns in this region force you to plant a flag on one side, lake or mountains, and commit. Tamworth lets you keep a foot in both without a punishing drive either way. It’s inland enough to feel like its own place, not a suburb of anything, and close enough to both worlds that you’re never actually cut off from either one.

Where to eat

The food scene here is all about quality over quantity, and I mean that as a compliment more than a caveat. You won’t have twenty dinner options. What you’ll have is a handful of dependable, well-loved spots, supplemented by whatever the farmers market and the farm stands are doing that week.

Rosie’s Restaurant is the practical local favorite, breakfast and lunch, homemade pie, the kind of diner where you’ll recognize half the room. Its the no-fuss version of Tamworth. The Other Bakery on Main Street, which most people still call Tamworth Bakery out of habit, is probably the strongest everyday stop in the village: good espresso, real bread, a savory lunch, Wednesday morning live music that turns into an informal town jam session. For a dinner out that would rival anything you’ll find on the Big Lake or in the Whites, Public House on Page Hill in Chocorua is the clear choice. Its a rustic gastropub with mountain views and a seasonal, locally sourced menu. Lots of people would say its not an every night place, but its probably the only place I ever order the chicken because its just that good. Everything else is great too, but the pan-roasted chicken never fails to delight.

Beyond that, its mostly insider knowledge. Sunnyfield Bakery sells bread through the farmers market and a few village shops rather than running its own storefront. White Gates Farm is worth knowing if you’re cooking for yourself and want to build a meal from what’s actually grown nearby. G III Deli on Route 16 is your reliable grab and go, full deli, pizza, beer, wine, long hours, not a destination so much as a relief when you need one. Songbird gives you familiar Chinese takeout. And Tamworth Distilling’s tasting room, open mainly Friday through Sunday, is a genuinely good place to sit by the river with a flight of something strange and delicious.

If I had one food day here, I’d start with coffee and an omelet at Rosies, hit the Saturday farmers market for the week’s produce, grab lunch at The Other Bakery, pop into the Distillery for a Gin cocktail for happy hour and then gorge myself at Public House on Page Hill for dinner. Good bread, farm food, a diner breakfast, and a truly excellent meal. That’s Tamworth’s food identity in a sentence: quality over quantity, and worth planning around rather than expecting to stumble into.

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The part where I confess

I sell real estate here. So there’s an obvious problem with a piece that opens by telling you to forget about this well-kept secret. I mean, I definitely want you all to come be my neighbors down the road…and maybe let me crash after an evening at the Barnstormers followed by a nightcap at the Distillery.

I’m not going to pretend the tension between being happy to help you find a home in Tamworth and not letting the Tamworth is Great cat out of the bag doesn’t exist. Truth is, I’m not worried about the right person finding Tamworth. I’m worried about too many people finding it. I’m worried about the version of this story where a place gets discovered the way a good trail gets discovered, and within a few years the thing that made it good is the thing that’s gone. Not because anyone did anything wrong. Just because enough people showed up wanting the postcard instead of the place, and the postcard is easier to buy into than the place is to keep.

So if you’ve read this far and you’re already picturing yourself at Rosie’s on a cold winter morning, or you know exactly why a town with two libraries for 2,800 people is a flex and not a fun fact, you’re probably not what makes me nervous. You’re the reason towns like this survive, not the reason they stop being themselves. Come learn the dirt roads. Go to town meeting. Don’t ask anyone to pave anything for your convenience.

🧭 Jenn

Keys to the Lakes

People contact me to talk about buying land all the time. Most of the time, they’re long term investors and they’re pretty knowledgable about what buying land means. Sometimes, they’re looking to see what a parcel they’ve been sitting on for a decade or so is currently worth. But sometimes, it’s a different conversation.

Every so often, a buyer I’ve been working with tells me some version of the same thing after we’ve seen a few houses together. They’ve been through six houses that were almost right. The kitchen was renovated but the layout made no sense. The bones were good but the price seemed way too high for the amount of renovations they would need to make to be excited about the home. The one they actually loved got outbid by cash before they finished their coffee.

So they start thinking about land instead. Sometimes they quote country music songs: just buy the dirt, they say. Build exactly what we want. No compromises, no previous owner’s decisions to undo, no inspection report full of things somebody else let slide for twenty years. And when you’ve been looking at houses in the high $700s, land can feel cheap and easy.

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I understand the appeal completely. I also think it’s worth saying clearly, before anyone gets too far into the daydream: land is not a blank slate. It just hasn’t told you what it costs yet. If real estate were a game, buying a house is poker and buying land is roulette. Poker rewards what you know. Roulette doesn't care what you know; the wheel was already weighted before you sat down, you just can't see how. That's land. The wetlands, the ledge, the soil that won't pass a perc test, all of it was decided a long time ago. You're not going to outwit the house; you’re just deciding whether you want to play.

I pulled five parcels currently for sale across Belknap and Carroll counties, priced from just under $100,000 to just under a million dollars. Not because acreage or location matter more than everything else, but because together they make the same point from different angles. The price of land and the cost of land are two different numbers, and the gap between them is where all the real decisions live.

Wakefield — 00 Leighton Corner Road, MLS #5101256, 6.57 acres, $99,900. This is the number that gets people excited, the one that makes land feel like the obvious answer to a house market that makes buyers feel defeated. And it’s a genuinely nice parcel: surveyed, wildlife and trails nearby, close enough to North Conway and the Seacoast to feel central rather than remote. But the listing itself notes wetlands on the property, with the buildable area sited outside the flood zone to work around them. Water source is listed as unknown. None of that means walk away. It means before this number means anything, you need a wetlands delineation and a real answer on where your well goes, because “outside the flood zone” and “easy to build on” aren’t the same sentence.

Sanbornton — Lot 9-1 Roxbury Road, MLS #5105403, 5.00 acres, $169,900. This one is freshly cleared and subdivided off Roxbury Road, which means nothing has been tested yet. No well dug, no septic designed, no proof that the ground under those trees will support the house you're already picturing. That puts you at a fork before you've even made an offer. Either you buy on faith, betting that a lot this size in this location will work out, or you pay to find out first, which means testing land you might not end up owning. A perc test in New Hampshire typically runs $750 to $1,900, sometimes more if the site needs multiple test holes. A well is the bigger unknown: this part of the state sits on granite bedrock, and a complete system, drilling, casing, pump, the works, commonly lands between $5,000 and $20,000, occasionally more if the driller has to go deep to hit water. Neither of those tells you what a septic system will ultimately cost to install once it's designed, only what it costs to find out if you can. That's the real choice on a lot like this: speculate and hope, or spend a few thousand dollars just to stop guessing.

Moultonborough — 00 Gilman Point Road (Unit/Lot 2), MLS #5102302, 8.38 acres, $195,000. This one has done more homework than the first two. It's surveyed, with 327 feet of road frontage, and it's already been perc tested with data on file good for a four bedroom system. That's not nothing. Somebody spent real money finding that out so you don't have to gamble on it. The tradeoff: it can't be subdivided further, so what you see is what you get. And the road access is a mix of association, private, and public maintained sections, which is worth understanding before you assume year round plow service is guaranteed. Public maintained means the town shows up. The other two mean someone else does, or nobody has agreed on it in writing, and you don't want to find that out in the middle of a February storm.

Meredith — Lot 1 Winona Road, MLS #5093680, 7.79 acres, $235,000. The most finished of the four. Surveyed, paved public road frontage, and the home site and driveway have already been cleared, which saves real money before you’ve broken ground on anything else. It’s close to the Meredith town docks and has beach access to Lake Winnipesaukee, though that access is for municipal residents generally, which is worth knowing before anyone pictures private waterfront that isn’t actually part of the deal. There’s also a current use penalty the buyer will owe at closing, a relatively minor but real additional cost before your builder has so much as drafted a site plan.

And then there’s the one that changes the whole conversation.

Wolfeboro — 580 C Pine Hill Road, MLS #5091791, 20 acres, $980,000. Nearly a million dollars, and it isn’t even a finished lot yet. It hasn’t been surveyed. It’s being offered as part of a planned subdivision that hasn’t happened, on what the listing calls a risk free reservation, meaning you’re securing your spot in a plan, not purchasing a parcel with drawn boundaries. At roughly $49,000 an acre, it’s priced well above everything else on this list, largely for the view and the proximity to town and the lake. But price per acre and readiness per acre are not the same thing. You can spend more money here than on any other parcel in this piece and still be, in the most literal sense, waiting to find out exactly what you bought.

That’s the thing nobody tells you when land starts to look like the easy way out of a frustrating house search. The sticker price is never the real number. Every one of these parcels needs a well, unless one exists. A septic system, designed and approved. A driveway, cleared and graded. Power brought in from the road, sometimes a significant distance. Permitting timelines that don’t care how ready you feel. And then the actual build, at construction costs that have not gotten friendlier in the last few years.

None of that makes land a bad idea. People do this well all the time, and it can become exactly the right answer when the existing housing stock genuinely can’t give you what you need. But it only works when you go in knowing the land is not the finish line. It’s the starting line, and the real number is whatever the finish line ends up costing once you get there. And it only works if you’re okay with a lot of unknowns and have the stamina, the disposition, and the budget to roll with the punches. Because I’ve never heard of a custom build that didn’t leave everyone involved just a little bit bruised and bloody.

This series has moved through water access, price tiers, waterfront, and now land itself, and the thread underneath all of it is the same: the number on the listing is never the whole answer. Next up, we’ll get back to standing structures with a look at what it actually takes to buy a property as a vacation rental investment.

If you’re circling the idea of building instead of buying, I’m always happy to walk through what a specific parcel would actually take to bring to life; the wells and the septic and the permitting and all of it, before you fall in love with an acreage number or a dream house design that doesn’t tell the whole story.

Here’s to knowing what you’re in for, or that you’re in for whatever happens.
🧭 Jenn

Keys to the Lakes