Wolfeboro

Wolfeboro bills itself as "The Oldest Summer Resort in America," and the claim holds up: Colonial Governor John Wentworth built a summer estate on nearby Lake Wentworth in 1769, making this the first vacation destination in the United States. The town sits at the eastern shore of Lake Winnipesaukee, New Hampshire's largest lake, and its compact downtown fills with visitors from Memorial Day through foliage season. Year-round, Wolfeboro is a real community — Huggins Hospital provides regional healthcare, Brewster Academy brings international boarding students to its 80-acre lakeside campus, and GI Plastek runs advanced injection-molding operations. Lake access defines daily life here, with Albee Beach and Cate Park offering public swimming and sandy shoreline on Winnipesaukee's eastern edge. Locals know about The Nick, a swimming hole on the Winnipesaukee River where generations have enjoyed cliff jumping into the deeper pools. The Wright Museum preserves WWII-era American history with a nationally significant military vehicle collection, while winter brings cross-country skiing at Abenaki and ice fishing on the lake. The population swells from roughly 6,300 to 15,000 in summer, and the local economy has adapted with marinas, restaurants, and shops that sustain the year-round tax base. This balance between seasonal tourism and permanent residents keeps Wolfeboro functioning as both a vacation destination and a working community where people actually live and raise families.