Portland, Maine


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Population: 140,000
Annual Household Income: $38,000
Median Home Price: $150,000
Climate: Foggy on land, windy on the water.

Portland may be the maritime epicenter of New England, but that is no longer its defining characteristic. In fact, its defining characteristic these days may be that it defies definition. It’s a place where lobstermen and lawyers (more of the latter per capita, locals claim, than any American city save Washington, D.C.) live side-by-side. Where your turn-of-the-century waterfront farmhouse is just minutes from the newly refurbished civic auditorium. Where the Old Port is anything but. And where you can spend the rest of your days lazily navigating around inlets and islands without dropping anchor at the same one twice.

THE HOME FRONT: The two major residential neighborhoods in town, the West End and Munjoy Hill, aren’t necessarily the best places to settle. Yes, there are old colonials oozing character (with prices averaging around $500,000), but the West End also tends to attract recent college graduates and those looking to pay $85,000 for a two-bedroom condo. Munjoy Hill, another haven for the young and struggling, is packed with old-style apartment houses and tightly sited city homes ($140,000). For more acreage and more family-oriented neighborhoods, consider the Scarborough area, where an occasional three-bedroom ranch can still be found for $98,000; three- to four-bedroom colonials list for $160,000. In nearby and ultraquaint Falmouth, prices rise steeply, to $350,000 and up. Falmouth Foreside, a ritzy enclave overlooking the sea, features stately Tudors and other New England mansions, some with widow’s walks and architectural bridges. These can fetch $2 million or more when they go on the market, which isn’t very often.

THE BACKYARD: Windjammer cruising, of course, is the unofficial state pastime. Most of the action happens out of Penobscot Bay, 100 miles north of town, and on Frenchman’s Bay, 160 miles north. Get even more intimate with Portland’s briny charms from the cockpit of a kayak. The coastline is so convoluted, and the offshore islands so plentiful, that you don’t have to cover great distances to do a lot of exploring. Join the corps of coastline stewards at the Maine Island Trail Association ($40 a year; 207-596-6456), and you’ll be part of an invaluable resource that provides exclusive island access. Not feeling nautical today? Try Mount Katahdin for solitary hiking in summer, Sugarloaf or Sunday River for festive skiing in winter.

NINE TO FIVE: No longer cargo shipper to the world, Portland doesn’t have too many professional Ishmaels left. The top three employers are the Maine Medical Center, UNUM Insurance, and L.L. Bean, with a number of big banks not far behind. True, there’s still a ship-repair facility on the waterfront, and the new Maine State Pier serves thousands more customers each year, especially as cruise ships like the QEII now dock in town.

ON THE TOWN: Once you get your personal lobsterfest out of the way, you’re free to concentrate on other diversions. The Old Port, after dusting off its image as the historic district, has become the trendy destination for a patchwork of restaurants and brew pubs that has put to rest the notion that “Portland nightlife” is an oxymoron. The city also offers a fair amount of food for the soul. Two-thousand-seat Merrill Auditorium brings in acts ranging from George Carlin to Yo-Yo Ma. Portland also boasts its own symphony and opera company and has recently played host to several international dance troupes. For homegrown fare, check out the Maine College of Art, which regularly (some say too regularly) shows off its students’ creations.

THE PRICE OF PARADISE: The private purchase of many formerly public coastal islands during the past 25 years has brought a not-in-my-backyard vibe to once laissez-faire island-hopping along the coast.


BEST OF THE REST BAYFIELD, WI: Gingerbread fence out front, Apostle Islands out back. PORT TOWNSEND, WA: Bathtub-size bank account buys Olympic-size view. ANTIGUA GUATEMALA, GUATEMALA: Cobblestones and coffee in the volcano-ringed highlands.