Westport's earliest settlers were farming families who called the area Green's Farm, part of the surrounding towns of Fairfield, Norwalk, and Weston. The town was formally incorporated on May 28, 1835, taking land from all three neighbors and adopting the name Westport. By the 19th century, the town had become a bustling shipping center and the leading onion-growing region in the entire country.

Around 1910, artists discovered Westport, and the town transformed into a nationally known center of creative life. The Famous Artists School and Famous Writers School both established roots here, drawing illustrators, writers, and creative talent from across America, and the population doubled within thirty years.

That creative legacy deepened through the 20th century. F. Scott Fitzgerald lived in Westport while working on The Great Gatsby, and decades later, Martha Stewart bought a run-down 1805 farmhouse on Turkey Hill Road in 1971, the property where she built her catering business and, eventually, her entire lifestyle empire over the following 36 years. Paul Newman and Joanne Woodward made Westport their home for decades, deeply intertwined with the Westport Country Playhouse's story.