Lake Winnipesaukee offers vacationing without a chain store in sight

The patio in front of the Yum Yum Shop is the place to be on a mellow morning in Wolfeboro, New Hampshire. A group of regulars — older men in shorts and polo shirts — relax in white Adirondack chairs, petunias spilling around them, as they hoist cups of coffee and debate world affairs between bites of date bars and doughnuts. Keeping an eye on them is the bakery’s iconic running gingerbread man, frozen in midstride on the blue and white sign, just as he has since 1948. 

Here on the southeast corner of Lake Winnipesaukee, in the town of Wolfeboro, you can get a latte and a whoopie pie, but not from Starbucks. You can have a tower of onion rings with a lobster roll fresh from the seacoast that’s only 90 minutes away, but you can’t get a McDonald’s burger. You can stay at a historic inn, but you can’t get a room at a Hampton Inn. 

Wolfeboro anchors the ragged ring that is Lake Winnipesaukee (WInni for short, for obvious reasons). It’s the largest lake completely within the borders of New Hampshire and, as visitors are informed repeatedly, Wolfeboro lays claim to the invented title of America’s original and oldest resort area. That’s due to the families of industry captains who streamed to this oasis of mountain cool from Boston, Portsmouth and even points south every summer beginning in the late 1700s. 

Since then, Winni has democratized recreation, with family-owned resorts and municipal beaches decorating its rocky shoreline. Visiting is less stepping back in time and more stepping into a parallel America that forgot to create franchises. 

With its piney shores and rocky ledges, the lacy perimeter of the lake makes a swift and efficient daytrip a challenge. It takes at least four state routes — 28, 11A, 106 and 109 — to start southwest from Wolfeboro and end up back in Wolfeboro. A more logical approach is to choose one of the larger villages — Wolfeboro, Meredith, Alton or Laconia — and spinoff daytrips from there. 

In September, my husband and I snagged one of the last day cruises on the venerable Mount Washington, a white, wooden Victorian-style pseudo-paddleboat that crisscrosses Winni from Wolfeboro to Weirs Beach and, occasionally, points in between. It was 70 degrees on the dock, but once in the middle of the sapphire lake, as a bracing breeze swept down from the actual Mount Washington (to the east), we were glad we’d brought windbreakers and sweaters. Clam chowder, lobster rolls and coffee were just the thing as the boat skirted islands so small that they were essentially boulders bearing pine trees like fragrant torches.  

Even on a bright yellow day, just a quiver before the birches turned golden and the maples blazed orange, the dark green of the pines cast deep shadows on the long lawns of quiet summer camps and trophy vacation cabins. The boat pulled into Weirs Beach, an apron of sand overlooked by ice cream stands, souvenir shops and shingled houses with beach towels flapping from their fences. A few people got off and a few people got on. Another hour across Winni and we were back at the Wolfeboro dock. Another time, we’ll come back for a sunset cruise. 

With its reliable waves of tourists, the Winnipesaukee region is a happy hunting ground for locally made crafts, especially blown glass and wood furniture. Now, visitors can center a visit around making their own souvenirs. Just opened in January, Makers Mill in Wolfeboro offers destination-worthy workshops for aspiring painters, sewers and woodcrafters. Intended to both draw visitors who want to experiment with new skills by way of recreation, and to support local entrepreneur-artisans with rental space and equipment, Makers Mill offers one more reason to anchor a week or long weekend in Wolfeboro. 

And in keeping with the New England spirit of making your own, Van Otis Chocolates in downtown Wolfeboro offers sweet fuel in the form of maple cream truffles and chocolate shaped in the state’s distinct stovepipe silhouette. As evidence of the eternal appeal of chocolate, the shop nudges the neighboring Yum Yum shop with a little Yankee one-upmanship: founded in 1935, it’s 13 years older.

Antique boat on Lake Winnipesaukee
Photo: Bob Kozlow, courtesy Lakes Region Tourism Association.

Getting There and Getting Around

From Concord, New Hampshire, take Rte. 28 northeast through fields and forests to Wolfeboro. 

Coming from the west, head for Tilton, New Hampshire. Its exit from Rte. 93 is the only mecca for chain retail and restaurants. Have lunch, though, at the Tilt-n Diner, a raucous throwback to the bobby-sock era. Part of the locally popular Common Man chain, you can indulge in the same rich clam chowder sold at that company’s ritzier locations. Fortified, head east on Rte. 3 to the hamlet of Laconia, which decorates the southwestern appendix of meandering Lake Winnipesaukee.  

If you center your visit in Wolfeboro, you can engineer a car-free weekend. Fly into the Manchester-Boston Regional Airport (MHT) and take a local car service, such as JCN Shuttle (603-515-1894) or Murphy’s Transport (603-340-0723) to get you to and from the airport. Plan a long weekend itinerary relying on the Mount Washington’s daily loop from Wolfeboro to Weirs Beach, kitty-corner across the lake, to explore the far side. Check the boat schedule, including mail boat ride-alongs, online. Have breakfast in Wolfeboro, a hot dog lunch at the Boardwalk Bar & Grill adjacent to Weirs Beach, and be back via the Mount Washington for dinner on the shore as the sun sets behind the White Mountains. Wolfeboro also offers all manner of canoe and kayak rentals and local outfitters for fly-fishing and hiking daytrips.

If You Go

As is the case at many seasonal destinations, Winni regulars book a year or more in advance, especially for summer and the short, bright October run of foliage. In the absence of chains, you’ll have to check with individual hotels and resorts to find open dates. The lake is studded with vacation rentals, many available through local agencies as well as national platforms like Airbnb and Vrbo. The Wolfeboro Inn sprawls on the northern perimeter of downtown and its spacious parking lot is the default drop-off and pickup spot for regional buses and tour groups. Another option is the Pickering House Inn has raised that bar with its luxury breakfast and Shaker take on modern décor.

Lakeview dining is the thing on Winni. Besides downtown Wolfeboro, which is studded with ice cream shops and diners, each little town has its own casual waterfront dining spot. One noteworthy addition, in late 2022, is The Breeze, at 25 Dock Road in Gilford. Elevated above an unlikely shoreline populated by boat repair shops and a public service marina, The Breeze offers surprisingly wide views and innovative twists on old classics. Right on the lake loop (though not on the water) are two solid dining standbys: in Wolfeboro, Morrisseys’ Front Porch for a hearty helping of New England seafood and on the western perimeter, in Meredith, Hart’s Turkey Farm Restaurant, which serves Thanksgiving goodness all year round. 

Top photo courtesy Mount Washington Cruises.

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