Wolfeboro

In contrast to the motorboats and mini-golf of the western shore, the eastern side of Lake Winni [1] is known as the quiet side. That reputation is bolstered by the quaint town of Wolfeboro, which is home to a whopping 5,500 people—most of whom came (and stayed) for its peaceful vibe and relaxed pace. They refer to their town as “the oldest summer resort in America”—a true, if somewhat vague, claim, based on the New Englanders who built homes here two centuries ago, after colonial governor John Wentworth built a summer home on what is now Lake Wentworth.

Wolfeboro today is as all-American as you can get, with flags waving on tree-lined streets and a plethora of historic homes harkening back with a sigh to a simpler time.

Nearby Ossipee and Alton are equally sedate. The former stands at the crossroads of the Lakes Region [2] and White Mountains [3] in the shadow of one of New Hampshire’s [4] most dramatic peaks, Mount Chocorua. Alton firmly anchors the southern end of Lake Winni with a blink-and-you’ll-miss-it town center and a gazeboed common overlooking Alton Bay.

Much of the local action is found on the lake and the Merrymeeting River, as well as Mount Major and Straightback Mountain, which are both magnets for hikers.