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.

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Fodor's Maine, Vermont, & New Hampshire: with the Best Fall Foliage Drives & Scenic Road Trips

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