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.

Philadelphia

Philadelphia is cheesesteaks (the Pat's vs. Geno's argument is mostly theater), the Italian Market, and the Liberty Bell sitting modestly in a glass pavilion. Murals are everywhere (the city runs the largest public art program in the country). The Eagles fans climbing light poles is folklore for a reason. The food scene punches way above its weight and the bar scene knows it.