The oldest resort town in America happens to sit on the shores of Lake Winnipesaukee. Families return to this WASP-y New England community year after year to escape the heat, and such famous lake lovers as Kurt Vonnegut, Paul Newman, Drew Barrymore, Jimmy Fallon, and Dustin Hoffman have also been known to rent and own homes here. Thanks to a crop of young summer renters, the scene here has lately felt like a less-stuffy country club; chefs are setting up shop, Lone Wolfe Brewing Company opened its doors, and bakeries like Stellaloona are whipping up a blueberry tart that alone makes the drive worth it.
While the lake is the main attraction, Wolfeboro also sees its share of festivals, farmers markets, and free concerts. The best day of the summer? Lobster Day at Hunter’s IGA Foodstore. A massive truck pulls up filled with lobsters and stays until it is empty. The price per pound can’t be beat — it’s pretty much a local holiday.