Bridgeport

Bridgeport

Bridgeport is the largest city in Connecticut, sitting on Long Island Sound with a working harbor and a real waterfront. P.T. Barnum lived here and the city's museum still pays tribute to his weird genius. It's a quick train ride to New York, with much cheaper housing and proper New England summers. The food scene punches above its weight, with old-school Portuguese and Brazilian spots packed every weekend.

Anchorage

Anchorage is the city where moose sometimes wander into downtown, the Chugach Mountains tower right behind your office, and summer days run 19 hours long. The Iditarod sled-dog race kicks off from here every March. The food scene leans heavily on the world-class salmon and halibut coming off the boats. Winter brings the northern lights flickering above the mountains and the kind of quiet you only find this far north. Wild edge.