🍁 Fall Weekenders

Music, Fairs, & Festive Things to Do In and Around the Lakes Region

Earlier this week we wrote about why we love Autumn up here—now let’s put that love to work. Below is your friendly, no-stress guide to the best autumn weekends within easy reach of the Lakes: music festivals, classic New England fairs, and a few food-and-drink happenings worth plotting into the calendar. We’ve called out what’s great for kids, where the food + drink scene shines, and where to expect live music.

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🎻 Two Music Events this Weekend

These are in Maine, but they’re both only about an hour away from Wolfeboro because when you live in the Lakes Region, Maine is right there.

Crooked River Gathering — Hiram, ME (Thu–Sun, Aug 28–31)

A four-day bluegrass/old-time gathering on a riverside fairground with camping, workshops/skill-shares (think sourdough, herbs, blacksmithing), artisan vendors, food trucks, and craft beer. Kids are welcome (there’s a kids ticket option) and there’s music day and night, plus campfire jams. Pro tip: bring camp chairs, layers, and cash for farm/artist vendors. crookedriverarts.org+1HumanitixMaine Public

• Kids: yes (family-friendly vibe, youth tickets)

• Food/Drink: food trucks + craft beer

• Live Music: wall-to-wall, including notable touring acts
  

  

LonesomeFest X’25 — Belgian Meadows Farm, Lebanon, ME (Sat, Aug 23; music noon–midnight)

A one-day roots/folk/Americana hang on a working farm (big shade tent, lawn space). Expect a full band lineup, BBQ + ice cream, and room for kids to romp; rough camping noted. If you like songwriter circles and rootsy sets, it’s your jam. ticketleap.eventsAllEvents

• Kids: yes (outdoor farm setting)

• Food/Drink: BBQ + treats on site

• Live Music: continuous sets all day

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🎡 Fairs = Peak New England

These are easy day trips from the Lakes and perfect multi-generational outings.

• Hopkinton State Fair — Contoocook, NH (Thu–Mon, Aug 28–Sept 1)
  Agricultural shows, midway rides, live entertainment, fair food, and the demo derby. A classic Labor Day tradition—arrive early for easier parking. Kids: huge yes. Food/Drink: classic fair staples. Live Music: daily. Hopkinton State Fair
  

• Deerfield Fair — Deerfield, NH (Thu–Sun, Sept 26–29)
  One of NH’s biggest ag fairs with barns, exhibits, midway, and plenty of apple-crisp energy. Kids: yes. Food/Drink: extensive vendors. Live Music: fairground stages. deerfieldfair.com
  

• The Sandwich Fair — Sandwich, NH (Sat–Mon, Oct 11–13; Columbus Day weekend)
  The Lakes Region’s hometown fair: 4-H shows, livestock, crafts, rides, and pumpkin-spice everything. Kids: yes (plan a full day). Food/Drink: tons. Live Music: daily fair entertainment. The Sandwich Fair
  

• Fryeburg Fair — Fryeburg, ME (Sun–Sun, Sept 28–Oct 5)
  Maine’s “blue ribbon classic”—massive grounds, harness racing, barns, and foliage views. Kids: yes. Food/Drink: huge vendor mix. Live Music: multiple stages. Maine

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🎃 Fall in the Lakes (and very nearby): Mark These

• Gunstock Labor Day Craft Fair — Gilford (Sat–Sun, Aug 30–31)
  Outdoor craft market at the base area; easy to pair with leaf-peeping rides up to the summit. Kids: yes. Food/Drink: on-site options. Live Music: check Gunstock’s events listings; their summer music series runs through early Oct. gunstock.comVisit NH
  

• Wolfeboro Fall Festival — Wolfeboro (Sat, Sept 27)
  A family-friendly town celebration—think activities, vendors, and downtown fun. Kids: yes. Food/Drink: local vendors. Live Music: typically, yes (watch the event page for the stage schedule). Wolfeboro Area Chamber of CommerceFacebook
  

• NH Highland Games & Festival — Loon Mountain, Lincoln (Fri–Sun, Sept 19–21)
  Pipes and drums, athletics, dancing, and Scottish food & drink—a signature White Mountains weekend and a great foliage kick-off. Kids: yes. Food/Drink: Scottish fare + bevvies. Live Music: continuous. NHSCOTLoon Mountain Resort

  

• Beveridge Oktoberfest on the M/S Mount Washington — from Wolfeboro (Sat, Oct 18; afternoon cruise)
  Craft-beer tasting cruise with multiple decks of live entertainment—super festive and foliage-forward on the big lake. Kids: this one skews adult (beer-centric). Food/Drink: craft beer festival. Live Music: yes. Mount Washington Cruises
  

• Laconia Pumpkin Festival — Downtown Laconia (Sat, Oct 25; day-into-evening)
  Thousands of carved pumpkins, live entertainment, vendors, kids’ activities, and the iconic pumpkin tower. Kids: absolutely. Food/Drink: loads of options. Live Music: multiple acts. nhpumpkinfestivalLaconia+1
  

• Great Waters “Concerts in the Clouds” — Castle in the Clouds, Moultonborough (through early Oct, evenings)
  Picnic on the lawn or grab food from trucks; music with a mountain-and-lake sunset backdrop. Kids: yes (ear protection for littles). Food/Drink: food trucks + cash bar. Live Music: headliners each date. greatwaters.org
  

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🧭 Quick Cheat Sheet (save or screenshot)

• Crooked River Gathering (Hiram, ME | Aug 28–31) — Kids ✓ | Food/Drink ✓ | Live Music ✓. Camping & workshops; bring layers/chairs. crookedriverarts.org

• LonesomeFest X’25 (Lebanon, ME | Aug 23) — Kids ✓ | Food/Drink ✓ (BBQ/ice cream) | Live Music ✓ (noon–midnight). ticketleap.events

• Hopkinton State Fair (Contoocook | Aug 28–Sept 1) — Kids ✓ | Fair food ✓ | Live Music ✓. Hopkinton State Fair

• Deerfield Fair (Deerfield | Sept 26–29) — Kids ✓ | Fair food ✓ | Live Music ✓. deerfieldfair.com

• Sandwich Fair (Sandwich | Oct 11–13) — Kids ✓ | Fair food ✓ | Live Music ✓. The Sandwich Fair

• Fryeburg Fair (Fryeburg, ME | Sept 28–Oct 5) — Kids ✓ | Fair food ✓ | Live Music ✓. Maine

• Gunstock Craft Fair (Gilford | Aug 30–31) — Kids ✓ | Food ✓ | Check music listings. gunstock.com

• Wolfeboro Fall Festival (Wolfeboro | Sept 27) — Kids ✓ | Local vendors ✓ | Live Music (TBA). Wolfeboro Area Chamber of Commerce

• NH Highland Games (Lincoln | Sept 19–21) — Kids ✓ | Scottish fare ✓ | Live Music ✓. NHSCOT

• Beveridge Oktoberfest Cruise (Wolfeboro | Oct 18) — Adults-leaning | Craft beer ✓ | Live Music ✓. Mount Washington Cruises

• Laconia Pumpkin Festival (Laconia | Oct 25) — Kids ✓ | Food trucks/vendors ✓ | Live Music ✓. nhpumpkinfestival

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Logistics & Little Local Tips

• Parking & lines: For fairs (Hopkinton, Deerfield, Sandwich, Fryeburg), plan to arrive near opening or late afternoon to reduce wait times. Many offer shuttle lots—check the event pages day-of for alerts.

• Weather game-plan: Fall evenings get chilly—pack a mid-layer, beanie, and a blanket if you’ll be at outdoor music.

• Cash still wins: Some craft and farm vendors are cash-preferred; ATMs can run dry on peak days.

• Kids strategy: Set meet-up points, snap a photo of kids’ outfits at arrival (helps if someone wanders), and bring ear protection for concerts.

• Pet policies: Most fairs allow service animals only—double-check the FAQs before you bring a pup.
  

Driving time sanity check: Lincoln/Loon (Highland Games) is ~1–1.5 hrs from central Lakes; Fryeburg is similar depending on your start; Hiram (Crooked River) is roughly 1.5–2 hrs. Build in foliage-traffic buffers on peak weekends.