Quietly upscale and decidedly preppy Wolfeboro has been a vacation getaway since Royal Governor John Wentworth built a home on the shore of Lake Winnipesaukee in 1768—hence its reputation as the country's oldest summer resort. Its waterfront downtown bursts with tony boutiques and eateries, while smaller Lake Wentworth—a few miles east—offers a quieter vibe. The century-old, white clapboard buildings of Brewster Academy prep school bracket the town's southern end.


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