Bridgeport, CT, United States

Bridgeport's train station may be a major transportation hub, but the city itself is a gritty, urban center with persistent challenges. The 1,453 parking spaces are frequently full, as the 950 state-owned spots struggle to keep up with commuter demand. And while the station connects residents to the Northeast Corridor, the frequent bureaucratic headaches of dealing with local government are a consistent source of frustration. One fatal train derailment in 1955 is a sobering reminder that safety is an ever-present concern. Overall, Bridgeport is a hardscrabble city that will appeal most to those seeking affordable living and reliable transit, but its gritty realities may prove daunting for the faint of heart.