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.

Greenville

Greenville built a city around a waterfall. The Reedy River drops right through downtown in Falls Park, with a suspension bridge curving over it that locals show off like a trophy. Main Street is a textbook of how to revitalize a small American city: brick, trees, patios, and a steady stream of festivals. BMW's largest factory in the world is a few miles up the road. The Blue Ridge foothills start just outside town.