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).
There's also a good wine and specialty foods shop called Treats (stock up here if you're heading north). Pack a picnic and take it down to the dock on Water Street, where you can watch the fishing boats, or grab a lobster roll from Red's Eats or the lobster shack nearby. Wiscasset has expanded its wharf, and this is a great place to catch a breeze on a hot day.