Best Towns 2010: Portland, Maine

Best Overall (East)

Portland's Old Port District     Photo: Woods Wheatcroft/Aurora

POPULATION 66,194
MEDIAN HOME PRICE $235,000
HOMETOWN HERO Adam Gardner, lead singer of the band Guster, local radio host, and co-founder of Reverb, a nonprofit dedicated to creating more-sustainable concerts and tours

THE LIVING: Portland is one of those rare places that really does combine small-town charm with big(ger)-city opportunities. But what we really love is the uniquely Maine mix of generational fishermen and young professionals, the latter lured here by the relatively low cost of living and (for Maine, at least) a diverse economy that includes everything from major financial and insurance corporations to media companies like our partner Outside TV. The cobblestones of Old Port are quaint but not too cute, the working harbor is gritty yet still gorgeous, and the seafood is always fresh: Bon Appetit recently named Portland America's Foodiest Small Town.

THE PLAYGROUND: Casco Bay and the outlying islands are perfect for sunrise paddles or sunset sailing. Roadies can get their fix at lunch on the 28-mile loop to Black Point. Mountain bikers can hit 18 miles of bony single- and doubletrack at nearby Bradbury Mountain State Park after work. You've got Class IV–V rapids on the Kennebec and Penobscot and, come winter, your choice of three resorts (Sugarloaf, Saddleback, and Sunday River) all within three hours. Of course, you can always just grab your longboard (and five-mil wetsuit) and join the hardy surfers at the breaks on Higgins and Scarborough beaches. This is Maine; they're out there year-round.

THE NEIGHBORHOOD: South Portland has the same Casco Bay view (plus the Portland skyline) but two distinct advantages: less congestion and bigger backyards. You can find hundred-year-old, three-bedroom New Englanders for $220K.

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