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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 American Indians continually sacked it. Many considered the region a somewhat dangerous frontier, but its potential for prosperity was so apparent that settlers came, despite the danger, to tap its rich natural resources.

Portland’s first home was built on the peninsula now known as Munjoy Hill in 1632. 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 boy threw a celebration firecracker into a pile of wood shavings; 1,500 buildings burned to the ground. Poet Henry Wadsworth Longfellow said at the time that his city reminded him of the ruins of Pompeii. The Great Fire started not far from where people now wander the cozy streets of the Old Port.

Despite all the calamity and destruction, the city of Portland has always had a great spirit. Each time the city has fallen, its residents have rebuilt—much like a phoenix rising from the ashes.

Portland Sights

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 metro area of 230,000 residents—one-quarter of Maine’s entire population. Portland and its environs are well worth a day or two of exploration.

Portland Reviews

Despite its small size, Portland is blessed with a variety of often exceptional restaurants and cuisines rivaling that of a far larger city. Part of that quality stems from Maine’s highly desirable quality of life, which attracts fine chefs that appreciate the intimacy and character of downtown and the availability of fine local ingredients.

Fresh seafood, including the famous Maine lobster, is still understandably popular and prevalent, but there are plenty more cuisines to be enjoyed. Diners can choose from waterfront seafood shacks, elaborate prix fixe French dinners, country Italian, Thai, Vietnamese, Japanese, Irish, Mexican, Mediterranean, and a fusion of many different cuisines. More and more restaurants are using local meats, seafood, and produce as much as possible, buying outside the area only when necessary; changing menus reflect what is available in the region at the moment. As sophisticated as many of these establishments have become, the atmosphere is generally quite casual; with few exceptions, you can leave your jacket and tie at home.

Smoking is banned in all restaurants, taverns, and bars in Portland.

Portland Hotel Reviews

As Portland’s popularity as a vacation destination has increased, so has its options for overnight visitors. Though several large hotels—geared toward high-tech, amenity-obsessed guests—have been built in the Old Port, they have in no way diminished the success of smaller, more intimate lodgings, of which there are plenty. Inns and B&Bs have taken up residence throughout the city, often giving new life to the grand mansions of Portland’s 19th-century wealthy businessmen. A few chain hotels have also slipped in; most are near the interstate and the airport.

You can expect to pay from about $70 a night for a pleasant room (often with complimentary breakfast), up to more than $400 for the most luxurious of suites. In the height of the summer season, many places have minimum-stay requirements for weekends and holidays; make reservations well in advance and inquire about off-season specials.


Portland has a nicely varied nightlife, with a great emphasis on local, live music and pubs serving award-winning local microbrews. Big, raucous dance clubs are few, but darkened taverns and lively bars (smoke-free by law) pulse with the sounds of rock, blues, alternative, and folk tunes. Several hip wine bars have cropped up, serving appetizers along with a full array of specialty wines and whimsical cocktails. It’s a fairly youthful scene in Portland, in some spots even rowdy and rough-around-the-edges, but there are plenty of places where you don’t have to shout over the din to be heard.

Portland Shopping

Trendy Exchange Street is great for arts and crafts browsing, while Commercial Street caters to the souvenir hound—gift shops are eager to sell Maine moose, nautical items, and lobster emblems emblazoned on everything from T-shirts to shot glasses.

Several art galleries bring many alternatives to the ubiquitous New England seaside painting. Modern art, photography, sculpture, pottery, and artful woodwork now fill the shelves of many shops, revealing the sophisticated and avant-garde faces of the city’s art scene.

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