One of the earliest settlements in the state of Maine, Kittery suffered its share of British, French, and Native American attacks throughout the 17th and 18th centuries, yet rose to prominence as a vital shipbuilding center. The tradition continues: despite its New Hampshire name, the Portsmouth Naval Shipyard is part of Maine and has been building U.S. submarines since World War I. It was founded in 1800 and built its first warship in 1815. It's not open to the public, but those on boats can pass by and get a glimpse.

Known as the "Gateway to Maine," Kittery has become a major shopping destination thanks to its complex of factory outlets. Flanking both sides of U.S. 1 are more than 120 stores, which attract hordes of shoppers year-round. For something a little less commercial, head east on Route 103 to the hidden Kittery most people miss: the lands around Kittery Point. Here you can find hiking and biking trails and great views of the water. With Portsmouth, New Hampshire, across the water, Whaleback Ledge Lighthouse, and the nearby Isles of Shoals, Kittery is a picturesque place to pass some time. The isles and the light, as well as two others, can be seen from two forts along or near this winding stretch of Route 103: Fort McClary State Historic Site and Fort Foster, a town park (both closed to vehicles off-season).

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