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.

Manchester

Manchester is built around the Amoskeag Mills, once the largest cotton mill complex in the world, now converted into apartments, restaurants, and offices along the Merrimack River. The downtown's grown into a real food and brewery scene. It's the largest city in New Hampshire (still relatively small) and a quick drive to the lakes, the mountains, or Boston. Plus there's no state income tax or sales tax.