Bridgeport's story begins in 1639, when English settlers arrived in an area already home to the Pequonnock, a band of the Paugussett people. Early settlement centered on farming and fishing around Black Rock Harbor, and the community grew under the names Newfield and Stratfield before taking the name Bridgeport in 1800, in honor of the first drawbridge built over the Pequonnock River. The town incorporated in 1821 and became a city in 1836.

Everything changed when the railroad arrived in 1840, transforming Bridgeport from a mercantile harbor town into a booming industrial center. Factories here produced sewing machines, carriages, brass fittings, saddles, and ammunition, and the city became known for companies like Singer Manufacturing, Remington Arms, and the Bridgeport milling machine. By 1853, Bridgeport had become the county seat of Fairfield County.

No figure looms larger over Bridgeport's history than P.T. Barnum. The famed showman made the city his home for 40 years, building four houses here and wintering his circus in town, and he served as the city's mayor in the 1870s. The Barnum Museum preserves his legacy today, and the annual Barnum Festival, running since 1949, still celebrates his larger-than-life story.