The Paugussett, an Algonguian-speaking nation, occupied much of western Connecticut prior to the arrival of European colonists, including a region from present-day Norwalk to West Haven, and from Long Island Sound inland for as far as they could navigate by canoe on the Housatonic and Naugatuck rivers. English settlers first arrived in Paugussett lands in 1638-39, establishing settlements in New Haven, Guilford, Milford, Stratford and Fairfield. Within a few years, the Paugussett had been divested by the colonists of the vast majority of their lands. A reservation was set aside in 1639 at Golden Hill, site of a spring sacred to the tribe, in present-day Bridgeport.

It was named for the Newfield or Lottery Bridge, which was built across the Pequonnock River, connecting the wharves on its east and west banks.

In 1875, P. T. Barnum was elected mayor of the town, which afterwards served as the winter headquarters of Barnum and Bailey's Circus and Buffalo Bill's Wild West Show.

The Frisbie Pie Company was founded in 1871 by William Russell Frisbie. The company was located on Kossuth Street in Bridgeport's East Side, where workers would toss around the pie tins while on their breaks. The activity made its way to nearby college campuses and eventually caught the attention of Wham-O, a California-based toy company who made a small spelling change to avoid trademark infringement before giving birth to the Frisbee.

Bridgeport was initially part of nearby Stratford, but was incorporated as its own town in 1821.

Bridgeport's extensive public park system led to its official nickname, "the Park City". The city's first public park was the westerly portion of McLevy Green, first set aside as a public square in 1806.

In the summer of 1915, amid increased labor demand for World War I, a series of strikes demanding the eight-hour work day began in Bridgeport. These strikes were so successful that they spread throughout the Northeast.

Subway was founded as Pete's Super Submarines. The first restaurant opened in Bridgeport's North End in 1965. It was renamed Subway two years later, and a second restaurant opened in Wallingford, Connecticut in 1974. The company has since expanded to become a global franchise.

Bridgeport is notable for having had a socialist mayor for 24 years. Jasper McLevy, who served from 1933 to 1957, was known for his fiscal restraint. When asked, after a snow storm, when the City would begin plowing snow, McLevy allegedly replied, "God put the snow there, let him take it away."

Bridgeport averages about 33 inches (85 cm) of snow annually, compared to inland areas like Hartford and Albany which average 45 to 60 inches (110-150 cm) of snow annually.