This agricultural community was named for Corsicana businessman Bryan T. Barry, who developed the land deeded for the townsite by early settlers Dave and Effie Wright. The Barry Post Office was established in 1886, the same year the St. Louis, Arkansas & Texas Railroad came through the town. The first post office was housed in the general store operated by Owen Taylor, who also was the town's first postmaster. Henry Allison later served as rural mail carrier for 40 years.
Early businesses in Barry included the First State Bank, which operated from 1909 until 1931, grocery stores, gas stations, drugstores, blacksmith shops, a newspaper office, a meat market, a cafe, and a hotel. In 1910, W. T. Woodruff and R. W. Varnell formed Woodruff and Co., which sold dry goods, hardware, and farm implements.
Settlers were attracted to the area by its rich farmland, and by 1920 most of the land had been cleared and planted in cotton. Barry's first cotton gin was established in 1899 by Dan McCammon, and E. Y. Jordan and Jack Hodge also operated early gins. Methodist and Baptist churches were organized by the end of the 19th century, and the Barry School, which opened in 1895, served the area until 1958.