This Quiet New Hampshire Town Is An Underrated Gem For Nature Lovers
Wolfeboro sits on the eastern shore of Lake Winnipesaukee, in the heart of New Hampshire's Lakes Region. Known as the country's oldest summer resort, the town runs on lakeside beauty and old-school recreation that hold up year after year. Hike the Cotton Valley Rail Trail or ride a historic trolley tour. Cruise the lake on a century-old mail boat route. Swimming and fishing and paddling all sit within minutes of the historic downtown.
Wolfeboro Waterfront, Town Docks, and Bandstand
The heart of Wolfeboro is the historic waterfront district known as the Wolfeboro Town Docks, which once welcomed steamships full of visitors escaping the heat and crowds of New York City and Boston for a summer retreat by the lake. The working docks still play a central role in the town's natural landscape today, with panoramic views of Lake Winnipesaukee, the Belknap Mountains, and the Ossipee Mountains. On a clear day, you can even see parts of New Hampshire's White Mountains in the distance. From downtown Wolfeboro, the benches near the Town Docks are the best spot to watch the sunset over Wolfeboro Bay after dinner and drinks at one of Wolfeboro's waterfront restaurants, such as the Back Bay Boathouse, the Wicked Loon, or Garwoods.
Another waterfront gathering spot is Cate Park, which hosts community events and free outdoor concerts throughout the summer. Bring blankets, lawn chairs, and picnic baskets, and enjoy the music coming from the open-air Wolfeboro Community Bandstand. The town also hosts the Great Waters Music Festival, where you can enjoy first-rate live entertainment all summer long in natural settings at Brewster Academy, as well as on the streets of downtown Wolfeboro, where you can play brightly painted pianos set throughout town.
Rail Trails, Trolley Tours, and Mail Boats
The old-timey resort town embraces its past with outdoor adventures sure to evoke nostalgia in even the most seasoned travelers. The 12-mile family-friendly Cotton Valley Rail Trail takes you on a scenic route through the New Hampshire countryside, connecting Wolfeboro to the nearby communities of Brookfield and Wakefield. Perfect for hiking and biking, the historic Boston & Maine Railroad corridor is dotted with heritage markers for history buffs and offers plenty of opportunities for wildlife viewing for nature lovers and photographers. Pack a picnic to enjoy en route, or rent a cruiser from E-Bike Expeditions, which includes a helmet, bell, and bike lock.
Another way to explore the historic resort town is on a narrated 45-minute vintage-style trolley tour offered by the Wolfeboro Trolley Company. No reservations are needed to take the hop-on-hop-off trolley tour aboard Molly the Trolley, which departs from the Information Center at Wolfeboro Railroad Station on the hour, or from the Wolfeboro Town Docks on the half hour.
Experience a tradition that is over a century old with a 2-hour cruise on Lake Winnipesaukee, where you can join the M/V Sophie C. on a mail-delivery trip to one of the 264 islands on the 71-square-mile lake. During the cruise, you'll make about 12 island stops as the skipper points out highlights along the way. Help the crew deliver mail bags to the waiting island residents, following the same route used for over 100 years. Mail boat tours are operated by Mount Washington Cruises, which also offers narrated scenic trips, Sunday brunch, and dinner cruises.
Swimming, Paddling, and Fishing
Wolfeboro offers easy access to swimming beaches, paddling coves, and shore fishing, all within minutes of downtown and in the region between Lakes Winnipesaukee and Wentworth. The best swimming holes near Wolfeboro include Brewster Beach and Carry Beach on Lake Winnipesaukee, Albee Beach on Lake Wentworth, and the beach at Wentworth State Park. The state park is an open, sandy lakeside park about 5 to 10 minutes by car from downtown Wolfeboro. The park spans 50 acres, giving you lots of space to stretch out a beach blanket and enjoy swimming, camping, fishing, or paddling.
Closer to town, Wolfeboro Bay is sheltered and surrounds the Town Docks, so you can easily slip a kayak, canoe, or stand-up paddleboard into the water and start paddling. Check out local outfitters like Dive Winnipesaukee for everything from 2-hour to weekly rentals on SUPs, wakeboards, tubes, and inflatables.
Fishing is another beloved pastime in the Granite State, which has a reputation among anglers for its variety of fish species and crystal-clear waters. For shoreline fishing, the waters around the Town Docks are ideal for bass, lake trout, and salmon. Cate Park offers easy shore access to try your luck at perch, while Lake Wentworth is the best for largemouth bass, smallmouth bass, yellow perch, and pickerel. Use the boat launch at Wentworth State Park and spend the day on the water. Finally, the nearby Smith River is a narrow waterway connecting Lake Wentworth to Crescent Lake, where you can drop a line from the banks.
Rainy Day Fun
One of the perks of Wolfeboro is that if you can't spend time in nature because of the weather, a scenic drive around the lake is always an option. Within half an hour, Moultonborough is home to the New Hampshire Boat Museum, which holds 2,500 artifacts in its collection, including vintage race boats, sailboats, and engines. Admission is included if you book a one-hour tour on the Millie B., a 28-foot replica of a 1928 triple-cockpit wooden boat from the golden age of boating to see magnificent lakeside mansions, historic boathouses, and the Loon Sanctuary, a 200-acre wildlife refuge on the lake's north shore. Back in town, Wolfeboro is also home to the Wright Museum of World War II. The museum includes exhibits on military tanks, weapons, and motorcycles from the US Navy, Army, and Air Force, everyday life in the 1940s, and outdoor garden spaces.
Nature and Nostalgia on the Shores of Lake Winnipesaukee
Despite its reputation as the "oldest summer resort in America," Wolfeboro remains one of the less crowded towns on Lake Winnipesaukee. Perfect for weekend getaways or a week-long family vacation, it has everything you want in a classic New England town. Stroll the historic Town Docks, watch sunsets over Wolfeboro Bay, enjoy free summer concerts at Cate Park, or attend performances during the Great Waters Music Festival. Best of all, Wolfeboro puts trails, lake cruises, beaches, paddling, and fishing within easy reach of its historic downtown.
