Travel Guide: Have an Old-Fashioned Summer Vacation in New Hampshire’s Lakes Region

Is there anything more quintessentially summer than a weekend on Winnipesaukee?

A breathtaking view from Lake Winnipesaukee’s shores. / Photo by Bobmanley/Getty Images

Whether your pleasure lies in doing it all or doing nothing at all, New Hampshire’s Lakes Region offers an escape packed with superlatives. Let’s start with the town of Wolfeboro, which bills itself as “America’s oldest summer resort.” The twee town centered around Lake Winnipesaukee has all of the usual waterfront diversions (including swimming sans sharks or jellyfish), but to really explore the area, you’ll want to get out on the water. A two-hour ride aboard the Sophie C., a U.S. mail boat and “the oldest floating post office in the country,” or a dinner cruise on the M/S Mount Washington will allow you to soak it all in.

Excursions off the region’s nearly 300 lakes and ponds, meanwhile, are virtually limitless: There are cafés, galleries, and shops aplenty, and we could easily pass a day at Black’s perusing tourist tat and essentials. An ideal day trip for families is the Squam Lakes Natural Science Center in Holderness, with its gardens, paths, and animals, followed by sandwiches at the Squam Lake Marketplace. A more-adult outing, meanwhile, is the beautiful Meredith Sculpture Walk, culminating in a stop at Hermit Woods Winery for a glass of something red, white, or blue(berry).

Those willing to work for their views will find plenty of trails in the mountainous terrain surrounding the lakes. Favorite hiking spots include Castle in the Clouds in Moultonborough, with 28 miles of paths meandering through 5,500 acres, and Belknap Mountain in Gilford, a moderately challenging climb through spruce forest to a 740-foot peak with sweeping vistas. Cyclists will delight in the Cotton Valley Rail Trail, a 12-mile path stretching from Wolfeboro to Wakefield that skirts woodland, wetland, and lakeshore.

When it comes time to take an après-adventure breather, sip your bliss in an Adirondack chair with lake views at Church’s Landing in Meredith—or kick back with an IPA at Lone Wolfe Brewing Co.’s outdoor beer garden. For dinner, choices run the gamut from the superb pub fare at Nolan’s Brick Oven Bistro to the New Woodshed, a more-formal option housed inside a restored post-and-beam barn in Moultonborough. Round out the evening with a double feature at the old-school Weirs Drive-In Theater, where you can sprawl out on a blanket and relish the fact that the only drama you’ll find for miles is on the screen.

A cozy room at the Pickering House Inn. / Photo courtesy of the Pickering House Inn

Getting There

The route from Boston follows 95 North, but just over the New Hampshire border cuts inland toward the White Mountains. A detour to poke around downtown Portsmouth or a side trip to view one of the most photographed peaks in the state, Mount Chocorua, is well worth the added travel time.

Staying There

Steps away from downtown Wolfeboro—the epicenter of summer on Lake Winnipesaukee—the Pickering House Inn’s 10 elegantly decorated rooms feature the amenities of a luxury hotel (smart TVs, concierge service, radiant heated bathroom floors) combined with the down-home charm of an old-fashioned New England B & B.