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.

Salem

Salem is the Oregon state capital, smaller and quieter than Portland (less than an hour north), with the Willamette River running through downtown and the surrounding Willamette Valley producing some of the best Pinot Noir in the world. The state capitol is topped by a gold-leaf pioneer statue. Cherry blossoms line the riverfront every spring. Affordable and underrated.