From its beginning as a west central Texas frontier community Winters grew from a retail support center for the surrounding agricultural community to a small-town railroad link to an oil, gas and manufacturing center. Settlement of the area of Winters began in the 1880s when two families, the Currys and the Bells, staked claim to the land one mile southeast of the present-day town. In 1889, a small schoolhouse was built on land that was given by land agent J.N. Winters. The community met in the completed schoolhouse to vote on the town name and Winters won. Winters already had significant cattle and feed production, and cotton added to their 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 to construct a railroad between Abilene and Ballinger. By 1909, the railway reached Winters. This railway, along with the rise of blacktop roads and the automobile, ushered in an era of prosperity and expansion for Winters.
In 1949, Winters benefited in particular from the findings of the Cree-Sykes Oil Field and Fort Chadbourne Oil Field. 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, the business handled all types of feeds for customers. Unlike other railroad towns, the city of 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 is still progressing and is economically viable.