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 the 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 the earliest days it was a cosmopolitan city, with a large free black population who 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 new 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 (Indians 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 a group of committed residents undertook the energetic redevelopment of the area now known as Old Port Exchange . Their success has revitalized the city, keeping it at the heart of Maine life but you shouldn't expect a hive of energy. Portland is simply a pleasant, sophisticated, and in places very attractive town, not a major urban center.
Thanks to the various fires, not all that much of old Portland survives, though various grand mansions can be seen along Congress and Danforth streets. The Wadsworth-Longfellow House/Maine Historical Society at 485-489 Congress St was Portland's first brick house when built in 1785 by Peleg Wadsworth, but owes its fame primarily to Wadsworth's grandson, the poet Henry Wadsworth Longfellow, who spent his boyhood here. The gallery has changing displays of state history and art (June-Oct Mon-Sat 10am-4pm, Sun noon-4pm; $6, gallery only $4; tours on the hour and half-hour, 45min).
The Portland Museum of Art at 7 Congress Square is a much more modern affair, built in 1988 by the I.M. Pei partnership (Tues, Wed, Sat & Sun 10am-5pm, Thurs-Fri 10am-9pm; Mon 10am-5pm Memorial Day-Columbus Day; tours at 2pm daily & 6pm Thurs-Fri; ; $6, free Friday 5-9pm). All parts of the museum give superb views over the bay; at times the collection seems subordinate to the design, which does not allow much room for extensive displays. The lower stories usually hold temporary exhibitions - though there's a lovely open-air garden café as well - while the works upstairs include a lively and flirtatious set of 1880s Winslow Homer engravings, some Andrew Wyeths, and an array of early nineteenth-century European ceramics commemorating heroes of the American Revolution.
For relaxed wandering, the restored Old Port Exchange near the quayside, between Exchange and Pearl streets, can be quite entertaining, with all sorts of redbrick antiquarian shops, specialist book and music stores (particularly on Exchange St), and other esoterica. Several companies operate boat trips from the nearby wharves: the Palawan , a vintage 58ft ocean racer, sails around the harbor and Casco Bay islands and lighthouses from DiMillo's Long Wharf off Commercial Street (daily in summer; 2hr trip; $20; tel 207/773-2163), and Bay View Cruises, 184 Commercial St, offers seal-watching tours (daily May-Oct; $10; tel 207/761-0496). Casco Bay Lines runs a twice-daily mail boat all year, and additional cruises in summer, to six of the innumerable Calendar Islands in Casco Bay, from its terminal at 56 Commercial and Franklin streets ($10.75; tel 207/774-7871, ). Long, Peaks and Cliff islands all have accommodation or camping facilities. If you follow Portland's waterfront to the end of the peninsula, you'll come to the Eastern Promenade , a remarkably peaceful two-mile harbor trail that connects to East End Beach, below the headland. Above the promenade, at the top of Munjoy Hill, at 138 Congress St, is the eight-sided shingled 1807 Portland Observatory (June -Sept daily 10am-5pm; $3), which affords an exhilarating view of the bay.
