Winters began as a west central Texas frontier community and grew from a retail support center for the surrounding agricultural community into a small-town railroad link and later an oil, gas, and manufacturing center. Settlement of the Winters area began in the 1880s when the Curry and Bell families staked claims to land one mile southeast of the present-day town. In 1889, a small schoolhouse was built on land given by land agent J.N. Winters, and the community met there to vote on the town name, choosing Winters. The community already had significant cattle and feed production, and cotton added to its growing economy. By the first decade of the 20th century, Winters was typical of small settlement communities on the west central Texas prairie. In 1907, residents lobbied for construction of a railroad between Abilene and Ballinger, and by 1909 the railway had reached Winters. The railway, together with the rise of blacktop roads and the automobile, brought an era of prosperity and expansion. In 1949, Winters benefited especially from the discovery of the Cree-Sykes Oil Field and Fort Chadbourne Oil Field, and oil and gas extraction continues to contribute to the local economy. Another Winters industry was the C.I. Green Milling and Grain Co., established in 1918 and handling all types of feeds for customers. Unlike other railroad towns, Winters was never laid out on a planned grid, but instead grew in response to the importance of agriculture, petroleum exploration, manufacturing, and transportation. After 125 years, the community remains economically viable and continues to progress.