Winchester, named for Winchester, Tennessee, is on a line of the Southern Pacific Railroad twenty miles northwest of La Grange in northwest Fayette County. The area was first settled in 1827 by John Ingram, who received a grant nearby on the Colorado River still known as Ingram's Prairie. The town itself was platted in 1857 by John Gromme on lands originally granted to E. Campbell and J. F. Berry in 1831. A post office was established in 1866, and by 1900 the town had eighteen businesses. As a shipping point on the Waco branch of the San Antonio and Aransas Pass Railway, the community served a wide area of prosperous farms. Due to improved roads and the decline of cotton farming, the number of businesses dropped to nine by 1950, and the population dropped to 220. By the 1980s the population was fifty, and the settlement had four businesses. Most of the surrounding farmland had reverted to pasture for cattle, and additional revenues came from oil production. Through 2000 Winchester still had a population of fifty.