Maine's largest city is considered small by national standards—its population is just 64,000—but its character, spirit, and appeal make it feel much larger. In fact, it is a cultural and economic center for a metropolitan area of 230,000 residents—almost one-quarter of Maine's entire population. It's well worth at least a day or two of exploration.A city of many names throughout its history, including Casco and Falmouth, Portland has survived many dramatic transformations. Sheltered by the nearby Casco Bay Islands and blessed with a deep port, Portland was a significant settlement right from its start in the early 17th century. Settlers thrived on fishing and lumbering, repeatedly building up the area while the British, French, and Native Americans continually sacked it. Many considered the region a somewhat dangerous frontier, but its potential for prosperity was so apparent that settlers came anyway to tap its rich natural resources.In 1632 Portland's first home was built on the Portland Peninsula in the area now known as Munjoy Hill. The British burned the city in 1775, when residents refused to surrender arms, but it was rebuilt and became a major trading center. Much of Portland was destroyed again in the Great Fire on July 4, 1866, when a flicked ash or perhaps a celebratory firecracker started a fire in a boatyard that grew into conflagration; 1,500 buildings burned to the ground.Today, there are excellent microbrew and restaurant scenes—many visitors come here just for the food—and a great art museum. The waterfront is a lively place to walk around well into the evening.
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Things You Can't Miss
Stroll the cobblestoned streets for a behind-the-scenes look (and sample bites) from restaurants where the farm-to-table movement actually began.
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The Sea Dogs are a farm team for the Boston Red Sox, and the stadium has a center-field lighthouse that pops up when a player hits a home run.
imagebroker / Alamy
The museum’s collection, in a building designed by I.M. Pei, includes international (Picasso, Matisse) and local (Homer, Sargent) luminaries.
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How to choose the ship that will guarantee you a good time at sea.
Portland takes its beer seriously — one reason it is often listed as a favorite of beer geeks nationwide. Sample for yourself at these two breweries.
Stillman Rogers / Alamy
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