Stratford's story begins in 1639, when Puritan leader Reverend Adam Blakeman and a group of families recently arrived from England settled the area then known as Cupheag, meaning "harbor" in the local Paugussett language. The settlement was renamed Stratford in 1643, likely after Stratford-upon-Avon or Stratford-le-Bow in England, and land titles were formally confirmed by patent in 1685. Stratford's original boundaries were vast, eventually giving rise to the towns of Trumbull, Shelton, and Monroe, along with parts of Bridgeport.

Early Stratford thrived on shipbuilding and oyster fishing, industries that sustained the town for generations along its Long Island Sound shoreline. The 20th century brought a defining transformation: on September 14, 1939, Igor Sikorsky flew the VS-300, the first practical helicopter in the world, launching an aviation legacy that continues at Sikorsky Aircraft today.

In 1955, Stratford became home to the American Shakespeare Theatre, an 1,100-seat venue on the Housatonic River that hosted legends like Katharine Hepburn, Paul Newman, James Earl Jones, and Christopher Walken during its heyday. The theater closed in the mid-1980s, and the building stood vacant for decades before being destroyed by arson in January 2019, though the site, now Shakespeare Park, remains part of the town's cultural memory and hosts a regular farmers market today.