Maine's largest city has capitalized on the gifts of its port history – the redbrick warehouse buildings, the Victorian shipbuilders' mansions, the narrow cobblestone streets – to become one of the hippest, most vibrant small cities in America. With a lively waterfront, excellent museums and galleries, abundant green space, and both a food culture and a brewing scene worthy of a town many times its size, it's worth much more than a quick stopover.
Set on a peninsula jutting into the gray waters of Casco Bay, Portland's always been a city of the sea. Established in 1633 as a fishing village, it grew to become New England's largest port. Today, the Old Port district is the town's historic heart, with handsomely restored brick buildings filled with cafes, shops and bars. The working wharves keep things from getting too precious or museum-like, though, as fishmongers in rubber boots mingle with well-heeled Yankee matrons.