Wolfeboro, New Hampshire · Lakes Region
What's happening in Wolfeboro
Updated October 2026
Concerts, markets, holiday happenings and winter festivals in Wolfeboro and around the Lakes Region. We check the dates with the organizers every month.
Plan ahead
The big annual events. Where organizers have posted next year's dates, they're here.
Fourth of July in Wolfeboro
July 4, with a morning parade and fireworks over Wolfeboro Bay · Next: Jul 4, 2027 (schedule TBA)
Brewster Academy Commencement
late May · Next year's dates aren't out yet
New England Pond Hockey Classic (Meredith)
early February, 3 days · Next: Feb 5 to 7, 2027
Lake Winnipesaukee Antique & Classic Boat Show (Wolfeboro Town Docks)
one Saturday in late July · Next year's dates aren't out yet
Great Meredith Rotary Ice Fishing Derby
mid-February, 2 days · Next: Feb 13 to 14, 2027
Sandwich Fair
Columbus Day weekend, 3 days · Next year's dates aren't out yet
Christmas in Wolfeboro and Festival of Trees
the parade is the Saturday after Thanksgiving, and the Festival of Trees runs two weekends in December · Next: parade Nov 28, 2026; Festival of Trees Dec 5 to 13, 2026 (preview gala Dec 3)
Village Players summer and fall shows
a musical in the spring, plays in summer and fall · Next: Arsenic and Old Lace, Jul 30 to Aug 8, 2027; Clue, Nov 5 to 14, 2027
Coming up
October 2026
Model yachting with the Back Bay Skippers
Tuesdays and Thursdays through October, 1 to 3 p.m., weather permitting
Back Bay, viewing from Bridge Falls Path, Wolfeboro
Watch the model sailboats race on Back Bay.
Wolfeboro Area Farmers Market (indoor season)
Thursdays from Oct 15 through mid-December, 2 to 4:30 p.m.
Abenaki Ski Lodge, 390 Pine Hill Rd, Wolfeboro
The market moves indoors for late fall, with the same local farmers and makers.
Brewster Academy Fall Family Weekend
Oct 16 to 17, 2026
Brewster Academy, Wolfeboro
It's for Brewster families, but expect a busy weekend in town.
Classic movie night: Psycho (Village Players)
Oct 24, 2026 · Evening; time TBA (September's movie started at 7 p.m.)
The Village Players theater, 51 Glendon St, Wolfeboro
Part of the Hollywood Firsts classic movie series, with a short intro before the film. Admission $7.
Last weekend of the season at Castle in the Clouds
Oct 24 to 25, 2026
Castle in the Clouds, Moultonborough
The regular season ends October 25. The trails stay open after that, but the trolley, ticket window and restaurant close.
The Barefoot Movement and Cold Chocolate (Wolfeboro Friends of Music)
Oct 24, 2026
Wolfeboro (see Friends of Music for time and venue)
A double bill.
Man of La Mancha (Village Players)
Oct 30 to Nov 8, 2026 · Fri and Sat Oct 30, 31, Nov 6, 7 at 7:30 p.m.; Sun Nov 1 and 8 at 2 p.m.
The Village Players theater, 51 Glendon St, Wolfeboro
The classic musical, with some adult themes. Tickets are $10, $25 or $45.
Dinner concert: Once An Outlaw
Oct 31, 2026 · Doors 5:30 p.m.
The Barn at The Inn on Main, 200 North Main St, Wolfeboro
Dinner plus a concert. Get tickets in advance.
Last day of the season at the Wright Museum
Oct 31, 2026
Wright Museum of World War II, 77 Center St, Wolfeboro
Last chance this year. The museum's season runs May 1 to October 31.
Trick or Treat at Clark Park
Oct 31, 2026 · 5 to 7 p.m.
Clark Park (Clark Museum, 233 South Main St), Wolfeboro
The Lions Club's Halloween trick-or-treat event.
November 2026
Last day of the trail season at Squam Lakes Natural Science Center
Nov 1, 2026
Squam Lakes Natural Science Center, Holderness
Last day to walk the live animal trail this year; it's open daily May 1 to November 1.
Kingswood Theater presents Peter Pan
Nov 20 to 22, 2026 · Shows at 2 p.m. and 7 p.m.
Kingswood Arts Center, 396 South Main St, Wolfeboro
A family musical put on by Kingswood Theater.
34th Annual Turkey Trot
Nov 21, 2026 · 8 a.m. to noon
Starts and ends at the Railroad Depot, Wolfeboro
Wolfeboro Parks and Rec's Thanksgiving 5K, with a kids' run too. Work up an appetite.
Classic movie night: Jurassic Park (Village Players)
Nov 21, 2026 · Evening; time TBA (September's movie started at 7 p.m.)
The Village Players theater, 51 Glendon St, Wolfeboro
Part of the Hollywood Firsts classic movie series. Admission $7.
Svetlana and the New York Collective (Wolfeboro Friends of Music)
Nov 21, 2026
Wolfeboro (see Friends of Music for time and venue)
An evening of jazz and swing.
Christmas in Wolfeboro Parade and Community Tree Lighting
Nov 28, 2026 · Parade 3 p.m.; Santa's Hut 4 to 6 p.m.
Main Street, Brewster Academy north to Mill St, Wolfeboro
Santa and Mrs. Claus ride in the parade and light the town tree.
The Nutcracker (Northeastern Ballet Theatre)
Nov 28, 2026 · 6 p.m.
Kingswood Arts Center, 396 South Main St, Wolfeboro
The full-length holiday ballet, Thanksgiving weekend.
December 2026
A Charlie Brown Christmas (Village Players)
Dec 4 to 6, 2026 · Fri Dec 4 and Sat Dec 5 at 7 p.m.; Sun Dec 6 at 2 p.m.
The Village Players theater, 51 Glendon St, Wolfeboro
A stage version of the TV special. Tickets go on sale in late October.
Wolfeboro Festival of Trees
Dec 5 to 13, 2026 · Sat Dec 5 and 12, 10 a.m. to 4 p.m.; Sun Dec 6 and 13, noon to 3 p.m.; Wed Dec 9, Pizza in the Pines, 6 to 8 p.m.
Wright Museum, 77 Center St, Wolfeboro
More than 100 decorated trees fill two floors of the Wright Museum, with music and dance every weekend. Santa and Mrs. Claus stop by Sunday, December 6, 11 a.m. to 2 p.m. Tickets at the door: $10 adults, $5 kids 4 to 10.
Eileen Ivers: A Joyous Christmas (Wolfeboro Friends of Music)
Dec 12, 2026
Wolfeboro (see Friends of Music for time and venue)
A Celtic Christmas concert.
Classic movie night: Toy Story (Village Players)
Dec 19, 2026 · Evening; time TBA (September's movie started at 7 p.m.)
The Village Players theater, 51 Glendon St, Wolfeboro
Part of the Hollywood Firsts classic movie series. Admission $7.
Abenaki Ski Area opening day Tentative
Dec 26, 2026
Abenaki Ski Area, Pine Hill Rd, Wolfeboro
The town ski hill hopes to open around December 26, weather permitting.
January 2027
Classic movie night: Westworld (Village Players)
Jan 23, 2027 · Evening; time TBA
The Village Players theater, 51 Glendon St, Wolfeboro
Part of the Hollywood Firsts classic movie series. Admission $7.
February 2027
New England Pond Hockey Classic
Feb 5 to 7, 2027
Lake Winnipesaukee, Meredith
275 teams on 26 rinks on the natural ice of Lake Winnipesaukee. Spectators welcome.
48th Great Meredith Rotary Ice Fishing Derby
Feb 13 to 14, 2027
Headquarters at Hesky Park, Meredith
New Hampshire's big ice fishing derby. Tickets go on sale online November 1, 2026.
Classic movie night: The Last Starfighter (Village Players)
Feb 20, 2027 · Evening; time TBA
The Village Players theater, 51 Glendon St, Wolfeboro
Part of the Hollywood Firsts classic movie series. Admission $7.
2nd Annual Winter Mingle (Wolfeboro Area Chamber)
Feb 25, 2027 · 5:30 to 8 p.m.
The Barn at The Inn on Main, 200 North Main St, Wolfeboro
A winter get-together with food, and everyone's invited.
April 2027
Come From Away (Village Players)
Apr 9 to 18, 2027 · Apr 9, 10, 11, 16, 17 and 18; times TBA
The Village Players theater, 51 Glendon St, Wolfeboro
The Tony-nominated musical about the small town of Gander, Newfoundland, on 9/11.
We get these dates from the organizers, but plans change, so check their link before you go.
For places to eat, walk and explore, see our local guide.