Bridgeport was inhabited by the Paugussett native American tribe at the time of its English colonization. The earliest European communal settlement was in the historical Stratfield district, along US Route 1; known in colonial times as the King's Highway. Very closeby, Mount Grove Cemetery was laid out on what was a native village that extended past the 1650s. It is also an ancient Paugusett burial ground.
The English farming community grew and became a center of trade, shipbuilding, and whaling. The town incorporated to subsidize the Housatonic Railroad and rapidly industrialized following the rail line's connection to the New York and New Haven railroad. The namesake of the town was the need for bridges over the Pequonnock River that provided a navigable port at the mouth of the river. Manufacturing was the mainstay of the local economy until the 1970s.
The showman P.T. Barnum was a resident of the city and served as the town's mayor in the late 19th century. Barnum built four houses in Bridgeport, and housed his circus in town during winter. The first Subway restaurant opened in the North End section of the city in 1965. The Frisbie Pie Company was located here, and Bridgeport is credited as the birthplace of the Frisbee.
After World War II, industrial restructuring and suburbanization caused the loss of many jobs and affluent residents, leaving Bridgeport struggling with problems of poverty and crime. In the 21st century, with the city being gentrified and other redevelopment, the city is attracting new residents and widespread interest. It has become a destination for cultural and sporting events.
The first documented English settlement within the present city limits of Bridgeport took place in 1644, centered at Black Rock Harbor and along North Avenue between Park and Briarwood Avenues. The place was called Pequonnock (Quiripi for "Cleared Land"), after a band of the Paugussett, an Algonquian-speaking Native American people who occupied this area. One of their sacred sites was Golden Hill, which overlooked the harbor and was the location of natural springs and their planting fields. (It has since been blasted through for construction of an expressway.) The Golden Hill Indians were granted a reservation here by the Colony of Connecticut in 1639; it lasted until 1802. (One of the tribe acquired land for a small reservation in the late 19th century that was recognized by the state. It is retained in the Town of Trumbull.)