Portland, Maine

Portland, once home to poet Henry Wadsworth Longfellow, sits along Maine’s southern coast and brims with history, character and authenticity. Dating from 1633, it has spent most of its days as a seaport, a pirate hideout, a rail hub and most recently as a popular tourist destination. With a thriving arts scene, a picturesque setting, a charming downtown, outstanding restaurants and a working waterfront, Portland shapes up as a place many retirees want to call home.

Mainers are a down-to-earth bunch, and these characteristics are abundant in Portland, although recent transplants from New York and Boston have brought an added touch of sophistication. Bon Appétit Magazine has named the city “America’s Foodiest Small Town” for its fresh seafood eateries, microbrewery beers, artisanal bakeries and some of the best breakfasts served anywhere in America. More money is spent per capita in Portland restaurants than in any other U.S. city except San Francisco and New York.

Portland’s delights are not just confined to the palate. The Old Port downtown district along the harbor is impossibly quaint with cobblestone streets, art galleries, restored 19th-century red brick buildings, green awnings and sidewalk cafes. The areas is a magnet for tourists and locals alike.

The city also boasts the Maine College of Art and Design, the Portland Museum of Art, the Portland Stage Company, the Maine Historical Society and Museum, the Portland Symphony Orchestra, the University of Southern Maine and a campus of the University of New England.

Ferry lines offer summer cruises around many of the 200 islands that sit just beyond Portland’s Casco Bay. Portland Head Light, just a few miles outside of city limits, is the most photographed lighthouse in North America. Summer produce markets, roadside apple cider stands, lobster bakes and antiquing are all part of the delightful ambiance of coastal New England.

East End Beach is Portland’s primary beach and has picnic tables and a boat launch. Nearby beaches include Crescent Beach and Willard Beach, which is dog-friendly. The city maintains an extensive network of walking and bicycling paths to encourage residents to get outside and exercise. Old Orchard Beach, 20 minutes south, is a funky summer playground (lots of arcades, carnival rides, food stands and an 1898 pier) with a honky-tonk feel to it.

Housing includes Cape Cods, Colonials, bungalows, Craftsmans, cottages and Victorian residences, many beautifully restored (Better Homes and Gardens has featured several). South Portland, a southern suburb, is the fastest growing area and has new construction.