Bridgeport owes its status as Connecticut’s largest city primarily to its river and harbor access, which propelled its industry starting in the early 19th century. Alas, in the latter half of the 20th century it fell on hard times, becoming one of the poorest cities in America, and attempts at urban renewal have resulted in waves of unfortunate architecture in place of historic buildings. Only now does the city seem to be coming around, with corruption finally cleaned up and a new waterfront development seemingly leading the city on the right track. True revival, however, still seems some ways off.

On the flip side is relatively sleepy Fairfield, next door. It never hit the big time that Bridgeport did, which may have ultimately been its saving grace. One of the state’s oldest settlements, it was originally named Fairfield because the farmers who moved there found its marshland ideal for raising cattle. And because it has always depended largely on farming, the town has stayed unusually scenic and industry-free. Add to all that the serenity of Fairfield’s lakes and beaches, and it’s little wonder so many city residents make the pretty town a weekend destination.