Bridgeport is the most populous city in Connecticut, and the fifth-largest city in New England. Bridgeport is located along Long Island Sound, at the mouth of the Pequonnock River. The weather is perfect year-round. The winters are a brisk 25 degrees and the summers never usually get hotter than 85 degrees. The cityscape is beautiful. This harbor city is surrounded by Pequonnock River and Yellow Mill Pond. Bridgeport offers lovely small town charm while providing all of the amenities of a bustling big city. You'll also find plenty of cultural sites, sporting events, restaurants and sight-seeing ventures.