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 art galleries, abundant green space, and a food scene worthy of a town many times its size, it's worth much more than a quick stopover.
On a peninsula jutting into the grey 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.
Congress St is the main thoroughfare through downtown, passing Portland's most imposing buildings: city hall, banks, churches and hotels. Commercial St, where many businesses are located, runs the length of the harbor. Two promenades (upscale Western and more workaday Eastern) frame downtown Portland at opposite ends of the peninsula. The West End neighborhood is home to an impressive collection of 19th-century mansions and the bulk of the city's charming B&Bs. In the east, Munjoy Hill is Portland's up-and-coming hipster enclave.