Both Kittery and York claim to be Maine’s oldest community. Technically Kittery wins, but York looks older . . . depending, of course, on which Kittery and which York you are talking about.  Kittery Point, an 18th-century settlement overlooking Portsmouth Harbor, boasts Maine’s oldest church and some of the state’s finest mansions. The village of Kittery itself, however, has been shattered by so many bridges and rotaries that it initially seems to exist only as a gateway, on the one hand for workers at the Portsmouth Naval Shipyard and on the other for patrons of the outlet malls strung along Rt. 1. However, don’t overlook the shops and restaurants around downtown Waterman Square, or the strolling and swimming spots along coastal Rt. 103.

In the late 19th century artists and literati gathered at Kittery Point. Novelist and Atlantic Monthly editor William Dean Howells, who summered here, became interested in preserving the area’s colonial-era buildings. Novelist Sarah Orne Jewett, a contributor to the Atlantic, spearheaded restoration of  the magnificent 18th-century Hamilton House in her hometown,  nearby South Berwick. Her friend Sam Clemens (otherwise known as Mark Twain), who summered in York, was involved in the effort to buy up that town’s splendid old school, church, burial ground, and abundance of 1740s homes, recognizing York as Maine’s oldest surviving community. In 1896 Howells suggested turning York Village's "old gaol" into a museum. At the time you could count the country's historic house museums on your fingers.