Quietly upscale and decidedly preppy Wolfeboro has been a resort since Royal Governor John Wentworth built his summer home on the shore of the lake in 1768. The town bills itself as the oldest summer resort in the country, and its center, bursting with tony boutiques, fringes Lake Winnipesaukee and sees about a tenfold population increase each summer. The century-old, white clapboard buildings of the Brewster Academy prep
school bracket the town's southern end. Wolfeboro marches to a steady, relaxed beat, comfortable for all ages.