Our Wolfeboro: where we send friends

Cotton Valley Rail Trail

12 miles of hard-packed trail on the old rail bed, from downtown Wolfeboro out to Wakefield, past two lakes, over trestles and through woods and wetlands. Great for walking, biking and strollers in summer, and for snowshoes, cross-country skis and snowmobiles once there's snow.

Mast Landing on Crescent Lake (about a 5-minute walk)

A little public boat landing on Crescent Lake, the lake you look out on from the house.

Wright Museum of World War II (about a 10-minute walk)

A surprisingly big World War II museum right on Center Street. Open every day from May 1 to October 31.

Bridge Falls Path (about a 20-minute walk)

A short, pretty path behind the old train station downtown, along Back Bay toward Wolfeboro Falls.

Downtown Wolfeboro (about a 20-minute walk)

Shops, coffee, restaurants, the town docks on Lake Winnipesaukee and, of course, ice cream.

Brewster Beach (Lake Winnipesaukee) (about a 5-minute drive)

The busy one in summer and the one that's open to everyone. It's where the town's swim lessons and swim team are, and there are picnic tables. It's also a great spot for the Fourth of July fireworks over Wolfeboro Bay.

Carry Beach (about a 7-minute drive)

Quiet and shallow, so it's good for little swimmers.

Albee Beach (Lake Wentworth) (about a 3-minute drive)

A quiet beach with picnic tables, right on the Cotton Valley Rail Trail. You can bike into town for lunch and ice cream, then ride back for a swim.

From Scratch Baking Co.

Our go-to bakery, at 36 Center Street, a 15-minute walk or a 2-minute drive. They're open Tuesday to Saturday, 8 a.m. to 5:30 p.m., but hours can change, so give them a call first.

Baked by the Lake Bread Company (about a 10-minute walk, or a 1-minute drive)

Our favorite sandwiches in town, plus breads, pastries and coffee, at 83 Center Street.

Harmony Coffee House (about a 20 to 25-minute walk, or about a 4-minute drive)

A cozy coffee house at 21 Central Avenue with a fireplace, Scandinavian and American treats and light bites. Open Monday to Saturday, 6 a.m. to 4 p.m.

The Bay Diner (about a 20 to 25-minute walk, or about a 4-minute drive)

A small, friendly diner at 5 North Main Street downtown, serving breakfast and lunch.

Baked by the Lake Bread Company (about a 10-minute walk, or a 1-minute drive)

Our favorite sandwiches in town, plus breads, pastries and coffee, at 83 Center Street.

Nolan's Brick Oven Bistro (a 25-minute walk, or a 5-minute drive)

Wood-fired pizza and Italian on North Main Street, open seven days a week, all year.

Wolfgang's Pizza Subs & More (a 15-minute walk, or a 1-minute drive)

Pizza and subs to eat in or take home, at 45 Center Street on the way into town.

Back Bay Boathouse (about a 30-minute walk, or a 4 to 5-minute drive)

Easygoing lunch and dinner on Back Bay at 51 Mill Street, with a kids menu. Open every day, 11 a.m. to 9 p.m.

Burnt Timber Brewing & Tavern (a 15 to 20-minute walk, or a 2-minute drive)

A family-friendly brewpub on Lehner Street, just off the rail trail, with farmhouse-style beers, cider and applewood-smoked BBQ. Kids are welcome, and dogs are welcome on the patio. Open Wednesday to Friday 4 to 10 p.m., Saturday noon to 10, and Sunday 11 to 4.

Bailey's Bubble (about a 20 to 25-minute walk, or about a 4-minute drive)

Scooping in Wolfeboro since 1954. It's a seasonal spot, so check that they're open.

Yum Yum Shop (about a 20 to 25-minute walk, or about a 4-minute drive)

A Wolfeboro bakery and ice cream parlor since 1948. Get the frosted gingerbread cookies they're famous for, plus donuts, bread, pies and ice cream. Open every day, all year, from 7 a.m. Closing time changes with the season.

Hunter's Shop 'n Save (about a 20 to 25-minute walk, or about a 4-minute drive)

The family-owned grocery store at 60 South Main Street, rebuilt and reopened in 2024 after a fire.

Harvest Market

Another grocery option in town.

Wolfeboro Area Farmers Market

Every Thursday. It's outdoors in the warmer months, then moves inside to the Abenaki Ski Lodge from 2 to 4:30 p.m., starting October 15 and running through mid-December.

M/S Mount Washington cruise (from the Wolfeboro town docks, about a 20 to 25-minute walk or about a 4-minute drive)

Narrated cruises around Lake Winnipesaukee that leave from Wolfeboro in season. This year they added a second Wolfeboro departure, and you can get off at Weirs Beach.

The Village Players (a 20-minute walk, or a 3-minute drive)

Wolfeboro's year-round community theater, in an 1888 church on Glendon Street. They put on a musical and a couple of plays every year, and there's a classic movie night about once a month ($7, popcorn available). Coming up: Man of La Mancha (October 30 to November 8, 2026), A Charlie Brown Christmas (December 4 to 6, 2026), and movie nights on October 24, November 21 and December 19.

Cate Park Bandstand concerts

Free Saturday-evening concerts (7 to 9 p.m.) by the town docks all summer (July 11 to September 5 in 2026). Bring a chair or a blanket.

Wright Museum of World War II (May to October)

Pop Whalen Ice & Arts Center (about a 5-minute drive)

The town's indoor rink, with public skating. The schedule's on the town website.

The Village Players (a 3-minute drive)

Catch a classic movie night or a show (dates above).

At The Oaks

Honestly, the house is pretty good on a rainy day: a two-player arcade, foosball, the piano, puzzles, toys and dress-ups, and a big screen for movie night.

Castle in the Clouds (Moultonborough) (about a 30-minute drive)

A historic mountaintop estate with big views over the Lakes Region. The mansion is open May 23 to October 25 this year, and the trails are open year-round.

New Hampshire Boat Museum (Moultonborough) (about a 35-minute drive)

Classic wooden boats and lake history. The main exhibits are now in Moultonborough. This year's season ended October 11, so it'll be back next spring.

Squam Lakes Natural Science Center (Holderness) (about a 50-minute drive)

Walk the live animal trail and meet New Hampshire's native wildlife up close. Open daily May 1 to November 1 this year.

Kancamagus Scenic Byway (White Mountains) (about 1 hour 10 minutes to the Conway end)

34 miles through the White Mountain National Forest. It's famous for fall color, and for good reason.

Gunstock Mountain Resort (Gilford) (about a 35-minute drive)

Skiing, snowboarding, tubing and Nordic trails in winter.

Spring (April to May)

Mud season first, then everything turns green. The Wright Museum opens May 1, the farmers market heads back outdoors, Castle in the Clouds opens late in the month, and the rail trail dries out for biking.

Summer (June to August)

Beach days, Mount Washington cruises, Saturday concerts at Cate Park, cones from Bailey's Bubble, and the Fourth of July parade and fireworks over Wolfeboro Bay. More at wolfeborochamber.com.

Fall (September to November)

Fall color on the rail trail and the Kancamagus, last chances at the seasonal museums and Castle in the Clouds, and the indoor farmers market starting mid-October.

Winter and the off-season (December to March)

Abenaki is the town's own little ski hill, open some weekday evenings and weekends. This season it's aiming to open around December 26, weather permitting. Skate at Pop Whalen, ski at Gunstock, or snowshoe the rail trail. The Brewster and Carry beach lots get plowed so you can get out on the ice (Albee's lot closes after the first snow). On New Year's Eve there's Last Night Wolfeboro. Plenty of shops close for the winter, along with Bailey's Bubble and the Wright Museum, so check before you go.