Portland, Maine

The largest city in Maine, Portland was founded in 1632 in a superb position on the Casco Bay Peninsula, and quickly prospered, building ships and exporting great inland pines for use as masts. A long line of wooden wharves stretched along the seafront, with the merchants' houses on the hillside above.

From its earliest days, Portland was a cosmopolitan city, with a large free black population that traditionally worked as longshoremen; great bitterness arose when Irish immigrants began to muscle in on the scene in the 1830s. When the railroads came, the Canada Trunk Line had its terminus right on Portland's quayside, bringing the produce of Canada and the Great Plains one hundred miles closer to Europe than it would have been at any other major US port. Some of the wharves are now taken up by sleek condo developments, though Custom House Wharf remains much as it must have looked when Anthony Trollope passed through in 1861 and said, "I doubt whether I ever saw a town with more evident signs of prosperity." Most of what he saw of the town was destroyed by an accidental fire in 1866 (Native Americans in 1675, and the British in 1775, had previously burned Portland deliberately).

Grand Trunk Station was torn down in 1966, and downtown Portland appeared to be in terminal decline – until, that is, a group of committed residents undertook the energetic redevelopment of the area now known as the Old Port. Their success has revitalized the city, keeping it at the heart of Maine life – though you shouldn't expect a hive of energy. Portland is quite simply a pleasant, sophisticated, and very attractive town, where one can experience the benefits of a large city at a lesser cost and without the hassle of crowds.