Luxury Hotel near Lake Winnipesaukee | Pickering House Inn

Favorite Things to Do in Wolfeboro

Take a classic New England town, perch it on the banks of New Hampshire’s largest lake, add spectacular views of mountain ranges across the water, surround it with fabulous hiking and cross country ski trails, sprinkle in some beaches, museums, concert venues and shopping, and the result is Wolfeboro, NH.

Known as “America’s Oldest Summer Resort,” Wolfeboro sits on the shores of Lake Winnipesaukee, the third largest lake in New England. During the off-season, Wolfeboro is a cozy community of a little more than 6,000 year-round residents. When the weather warms up (or the ice fishing derby is happening!), the population swells five-fold as second homeowners return to their vacation properties and visitors come to enjoy the area’s stunning beauty and plentiful activities.

Whether you enjoy arts and culture, outdoor activities, or shopping and dining, the perfect adventures await in the Wolfeboro area. We’ve shared a few suggestions at the links below. When you are a guest at Pickering House Inn, we look forward to helping you plan the perfect visit and assisting with any reservations you may require.

[Please note that some of the attractions suggested below may be closed during the COVID pandemic. Please confirm operating hours before heading out!]

Lake Winnipesaukee & Lake Wentworth

At more than 70 square miles, Lake Winnipesaukee is the giant of New Hampshire’s lakes – and the focus of recreational fun in the region. Boating, fishing and swimming in warm weather gives way to ice fishing and snowmobiling in the winter. Of course, just gazing at the lake’s beauty keeps many a visitor and resident occupied year-round! Wolfeboro’s Lake Wentworth is a perfect spot for kayaking or spending a day at beautiful Albee beach.

Local Tip:
Ride the Millie B, a 28-foot, mahogany, triple cockpit “woodie” operated by the New Hampshire Boat Museum

Downtown Wolfeboro

Browse the eclectic shops lining the main streets in downtown Wolfeboro (you’ll find everything from fine art and upscale gifts to scuba and fishing gear), grab a bite to eat, or just watch the boat traffic come and go from the downtown docks. In warm weather, you can catch free concerts in the lovely Cate Park, perched right on the waterfront.

Local Tip:
Don’t miss the amazing ice cream at Bailey’s Bubble, a Wolfeboro institution

Outdoor Trails

Soak in the stunning scenery and get a great workout on the area’s wonderful hiking, biking and cross country ski trails! Enjoy breakfast at the Inn then walk downtown to hop on Bridge Falls Path, which connects you to the 11-mile Cotton Valley Rail Trail. The Lakes Region’s Ossipee mountain range offers an extensive network of trails, many of which offer gorgeous views of the lakes below.

Local Tip:
Hike, bike, snowshoe or ski from Wolfeboro to Wakefield on the rail trail from downtown Wolfeboro

Sports Facilities

Wolfeboro’s Abenaki ski area was founded in 1936, making it the oldest small ski area in America. It offers affordable skiing on seven trails from green to black diamond, glade skiing, night skiing and a terrain park. The adjacent Pop Whalen Ice & Arts Center is a favorite skating venue when conditions for outdoor skating are not ideal. In warm weather, the Kingswood Golf Course up the street from Pickering House Inn beckons golfers to its classic Donald Ross (18 hole – par 72) championship course open to the public.

Local Tip:
Enjoy spectacular views of the White Mountains, rolling grass pastures and beautiful woodland trails on horseback at High Meadow Farms


Wolfeboro’s natural beauty is its calling card, but there is much more to the area than meets the eye. Fascinating museums including the Wright Museum of World War II, the Libby Museum of Natural History, the NH Boat Museum and the Clark Museum complex of historic buildings are tucked throughout the area.

Local Tip:
Visit all four museums, plus travel by antique boat and Molly the Trolley with the Museum Loop

Arts & Culture

The Wolfeboro area is home to many artists, musicians and performers who are drawn to the tranquility and inspiring scenery of the region. Works from local artists are often displayed in downtown galleries and nearby Laconia and Plymouth are popular spots to catch both local and national musicians. The free concerts at Cate Park in downtown Wolfeboro are a summer tradition, as is the Great Waters Music Festival, which attracts outstanding performers of jazz, folk, classical, popular and Broadway music. During summer evenings, you can even enjoy music from the Cate Park concerts while relaxing on the porch of Pickering House Inn when you are our guest!

Local Tip:
Wolfeboro Art Walk features open art galleries, street performers, refreshments and more the last Saturday of every month from May-September.


Wineries and breweries are tucked throughout the Lakes Region. If you are craving a great craft beer, you need look no farther than Wolfeboro’s own Lone Wolfe Brewing Company, Burnt Timber Brewing and the tap room at Beveridge Craft Beer & Soap right downtown. New wineries are sprouting up in the area and the nationally recognized Tamworth Distillery is a short drive away (watch for tasting events at Pickering House Inn!)

Local Tip:
Tamworth Distilling in nearby Tamworth, NH offers a wonderful retail space and tasting bar in a beautiful building. Taste the full line of spirits , shop for cocktails and grab a quick bite to eat at the distillery’s café a quick walk down the road.

Markets & Festivals

Farmer’s markets, music festivals, antique boat and car shows, pond hockey tournaments, fishing derbies, a legendary 4th of July parade and a full calendar of other special events keep Wolfeboro hopping. Check our events calendar to see what’s happening during your visit.

Local Tip:
Wolfeboro’s farmer’s market is the place to go for fresh produce, handcrafted items, treats and live music on Thursdays from June until early October and on select dates in the winter

Easy Day Trips

Wolfeboro is ideally located in the heart of the Lakes Region, within an easy drive of New Hampshire’s White Mountains to the north or the New Hampshire and southern Maine seacoast to the east. Of course, there is so much to do right here in the Lakes Region, you may not want to roam farther afield. No matter the season, you can’t beat a leisurely drive all the way around Lake Winnipesaukee. The 60+ mile drive is a great way to explore all the Lakes Region towns along the way!

Local Tip:
Tour, hike and eat at Castle in the Clouds, an Arts and Crafts style estate built in 1913 on a mountaintop with stunning views of the lakes below. The mansion is surrounded by 28 miles of hiking trails on more than 5,300 acres. If hiking is not your style, you can always relish the view from a lovely dining patio.