Wiscasset

Settled in 1663, Wiscasset sits on the banks of the Sheepscot River. It bills itself "Maine's Prettiest Village," and it's easy to see why: it has graceful churches, old cemeteries, and elegant sea captains' homes (many converted into antiques shops or galleries).

Pack a picnic and take it down to the dock, where you can watch the fishing boats or grab a lobster roll from Red's Eats or the lobster shack on the dock. Wiscasset has expanded its wharf, and this is a great place to catch a breeze on a hot day. U.S. 1 becomes Main Street, and traffic often slows to a crawl. If you park in town, you can walk to most galleries, shops, restaurants, and other attractions. Try to arrive early in the morning to find a parking space—you'll likely have success if you try to park on Water Street rather than Main.