Weston's first English settlers in the early 1700s were mostly farmers living to the southeast in the Town of Fairfield, the boundaries of which extended to Weston until the late eighteenth century. In 1787, the North Fairfield parish was created in the area now occupied by the towns of Weston and Easton. In 1845, North Fairfield was split into the two towns and Weston was created.
Despite the rocky soil, farmers in town grew apples, onions and potatoes and grist, cider, lumber and fulling mills were built. The town had nine manufacturers by 1850, but two decades later only the Bradley Edge Tool Company still thrived. That factory burned down in 1911.
Unlike other nearby towns, Weston never had a railroad built through it, which hurt non agricultural businesses, so between the Civil War and the Great Depression, the town's population dropped from about 1,000 to a low of 670 by 1930. Artists, writers and actors from New York then became attracted to the community and began settling in it. Construction of the Merritt Parkway, which arrived just to the south of Weston in 1938, resulted in population growth.
