The Best of Summer in Wolfeboro
When the warm months arrive, Wolfeboro transforms into everything a New England summer should be. The lake sparkles, the patios fill up, and the calendar overflows with things to do. Whether you're planning a week-long vacation or a quick weekend getaway, these are the 10 experiences you won't want to miss.
1. Swim at Wolfeboro's Beaches
Wolfeboro is blessed with four public beaches, each with its own personality. Wentworth State Beach is the most popular—a sandy stretch on Lake Wentworth with lifeguards, picnic areas, and a bathhouse. Albee Beach, also on Lake Wentworth, offers a quieter setting that's great for families with young children.
For Lake Winnipesaukee swimming, head to Brewster Beach, a locals' favorite with stunning views of the Ossipee Mountains, or Carry Beach, a small gem tucked along the shore. Pack a cooler, bring a towel, and settle in—this is summer at its simplest and best.
Tip: Arrive before 11 AM on weekends to claim the best spots. Weekdays are significantly less crowded.
2. Cruise Lake Winnipesaukee
Seeing the lake from the water is a completely different experience, and Wolfeboro offers two excellent ways to do it. The M/S Mount Washington is the grand dame of Lake Winnipesaukee—a 230-foot historic cruise ship that's been carrying passengers since 1872. The scenic cruise from Wolfeboro offers panoramic views of the surrounding mountains and islands.
For something more intimate, the Mail Boat tour is a true local treasure. You'll ride along as the captain delivers mail to island residents, weaving through narrow channels and pulling up to private docks. It's a one-of-a-kind experience you won't find anywhere else in the country.
Tip: Book the Mail Boat in advance—it's a small vessel and sells out quickly during peak season.
3. Watch the Sunset from the Town Docks
Ask anyone in Wolfeboro for their favorite summer ritual and most will say the same thing: sunset at the Town Docks. Located at the heart of downtown where Main Street meets the lake, the docks offer an unobstructed view across Lake Winnipesaukee as the sky turns gold, pink, and purple.
Grab an ice cream from one of the nearby shops, find a seat on the dock or along the seawall, and watch the boats return to harbor as the sun dips behind the mountains. It's free, it's beautiful, and it perfectly captures the spirit of a Wolfeboro summer.
Tip: The best sunsets tend to happen from late June through August. Arrive 30 minutes before sunset for the best vantage point.
4. Bike or Walk the Cotton Valley Rail Trail
The Cotton Valley Rail Trail is a 12-mile multi-use path that follows a historic railroad bed from Wolfeboro to Sanbornville. The flat, well-maintained gravel surface makes it accessible to walkers, joggers, cyclists, and families with strollers.
In summer, the trail is shaded by a canopy of trees for much of its length, making it a cool retreat even on hot days. You'll pass through woods, along wetlands, and across open meadows with mountain views. Start at the Wolfeboro Depot trailhead downtown and go as far as you like—even a short out-and-back is rewarding.
Tip: Rent bikes in town if you didn't bring your own. The full trail is 12 miles one-way, but the first 3-4 miles from Wolfeboro are the most scenic.
5. Catch a Free Concert at Cate Park
All summer long, Cate Park comes alive with free outdoor concerts at the lakeside bandstand. The park sits right on Wolfeboro Bay with the mountains as a backdrop—it's hard to imagine a better setting for live music.
Bring a blanket or lawn chairs, spread out on the grass, and enjoy everything from jazz and blues to folk and classic rock. The concerts draw a wonderful mix of locals and visitors, and the atmosphere is relaxed and welcoming. Kids can play on the nearby playground while the music plays.
Tip: Check the town's summer events calendar for the weekly concert schedule. Arrive early for the best lawn spots closest to the bandstand.
6. Browse the Wolfeboro Farmers Market
Every Thursday during the summer, the Wolfeboro Farmers Market sets up with 30+ vendors offering local produce, baked goods, artisan crafts, fresh flowers, maple syrup, and handmade goods from across the Lakes Region.
It's more than just shopping—it's a social event. Grab a fresh-baked pastry and a cup of coffee, sample local honey and cheese, and chat with the farmers who grew your food. The market is a wonderful window into the agricultural heritage of rural New Hampshire.
Tip: The most popular items sell out early. Arrive when the market opens for the best selection, especially for baked goods and fresh berries.
7. Explore Castle in the Clouds
Castle in the Clouds is one of those places that feels almost too beautiful to be real. This mountaintop estate sits 750 feet above Lake Winnipesaukee, offering some of the most spectacular views in all of New Hampshire. The 1914 Arts and Crafts mansion is surrounded by 5,500 acres of conserved land.
Tour the historic castle, then spend the afternoon hiking the estate's trail network through forests and past waterfalls. The on-site restaurant serves lunch with panoramic lake views. For a full day trip, combine the castle visit with a hike to one of the property's scenic overlooks.
Tip: Allow at least 2-3 hours for the castle tour and a short hike. The drive up the mountain is scenic in itself—take it slow and enjoy the views.
8. Dine on a Lakeside Patio
Summer dining in Wolfeboro means eating outdoors with a view. The town has an impressive collection of restaurants with patios and decks overlooking the water—far more than you'd expect for a small New England town.
Garwoods is a waterfront staple with a sprawling deck right on Wolfeboro Bay—perfect for casual lunches and sunset dinners. Dockside Grille offers lakeside seating where you can watch boats come and go. For a more historic atmosphere, Wolfe's Tavern at the Wolfeboro Inn has been serving guests since 1812 and features charming outdoor seating.
Tip: Make reservations for dinner, especially on weekends and holidays. Lunch is usually easier to get a table, and the views are just as good.
9. Attend the Great Waters Music Festival
The Great Waters Music Festival is one of the cultural highlights of summer in the Lakes Region. This acclaimed series brings world-class musicians to Wolfeboro for performances spanning classical, jazz, folk, pop, and more.
The intimate venue and high caliber of performers make this a truly special experience. Past seasons have featured nationally recognized artists in a setting that feels personal and connected. It's the kind of event that makes a summer trip to Wolfeboro memorable long after you've gone home.
Tip: Popular shows sell out well in advance. Check the season lineup and purchase tickets early if you see a performer you love.
10. Visit the Wright Museum of World War II
The Wright Museum of World War II is one of New England's premier military history museums, and it's right here in Wolfeboro. The museum tells the story of the American home front during WWII through immersive exhibits, authentic artifacts, and an impressive collection of over 20 military vehicles including tanks, jeeps, and artillery pieces.
What makes the Wright Museum special is its focus on how everyday Americans contributed to the war effort—from victory gardens and ration books to factory work and community sacrifice. The exhibits are engaging for all ages, and the museum hosts a popular summer lecture series with historians and veterans. It's a meaningful way to spend a few hours, especially on a rainy day.
Tip: The museum is open May through October. Allow 1-2 hours for a full visit. Check their events calendar for the summer lecture series schedule.
Making the Most of Your Summer Visit
The beauty of Wolfeboro in summer is that you can mix and match these activities to create your perfect day. Start with a morning swim, bike the rail trail before lunch, eat on a lakeside patio, and end the day watching the sunset from the docks. Or take it slow—pick one or two activities and spend the rest of the day simply soaking in the atmosphere of this classic New England lake town.
However you spend your time, you'll quickly understand why generations of visitors have been coming back to Wolfeboro every summer since 1768.
