Webster, reported to be one of the oldest settlements in Wood County, was at a site west of State Highway 37 three miles southwest of Winnsboro and twelve miles northeast of Quitman in the northeast part of the county. The settlement apparently dates to 1854, when Gilbert Smith Matthews acquired the site and named it after the statesman Daniel Webster. According to some sources, however, the area was known as Prospect Hill in 1855 when it received its first post office. By January 1856 the post office name had been changed to Webster, and the town was said to have had a larger population than Dallas in the late 1850s. Before the Civil War a store at Webster run by Robert Bradshaw, Matthews's son-in-law, was said to be one of the largest in Wood County. The town's businesses at that time also included two wholesale houses that shipped by wagon from Jefferson to Sulphur Springs, Greenville, and Dallas via their storage buildings in Webster. When in 1876 the East Line and Red River Railroad came through Winnsboro, Webster's businesses moved to the railway town, and by 1881 Webster's post office had closed. In 1896 the community's two one-teacher schools enrolled seventy-three White students and sixty-two Black students; ten years later the student populations remained about the same. By the early 1930s Webster school district's seventy-three White students received nine grades of school from three teachers; forty-seven Black students received eight grades of school from two teachers. In the 1940s the community had a church, a school, and a number of dwellings. By 1960 the church and school had disappeared, and all that remained at the site were a few dwellings scattered less than a mile southeast of the Winnsboro oilfield. Webster does not appear on the 1988 highway map.
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