Chester is near the junction of U.S. Highway 287 and Farm Road 1745, thirteen miles northwest of Woodville in extreme northwestern Tyler County. The townsite is part of a five-league grant made to Gavino Aranjo on the old road from Nacogdoches to Liberty. In 1883 the Trinity and Sabine Railway routed its new line through the area one mile south of Peach Tree Village. Lots were sold near the line, and soon the Peach Tree Village post office and the Mount Hope Masonic lodge moved to the new town of Chester on the railroad. The town was named for Chester A. Arthur, who was at the time a senator from New York. The first postmaster at Chester was A. B. Green, who had been postmaster in Peach Tree Village. W. B. Carnes had a mercantile business in the town, and Dr. Whitehead of Mount Hope set up his son with a store there as well. Tom Seamans had a blacksmith shop, John Cobb a saloon, and Bill Lee a boardinghouse, where he also worked as justice of the peace. Jackson Riley had a large hotel, and John Lowe was constable. By 1890 the town had a sawmill, a school, two gins, and two churches. The population of Chester was reported as 176 in 1904, 300 in 1914, and as 250 from the mid-1920s to the mid-1940s, when it rose to 350. It continued to be reported at that level until the late 1960s, when it dropped to around 260. By 1980 the population had risen to 301, and by 1988, to 409. The community generally had from seven to ten rated businesses during this period. The local blackland soil is fine farmland; Chester in the 1980s was also surrounded by prime pine forests and for many years had seen sawmill activity. In 1986 the town comprised farmers and cattle raisers, three churches, several stores, substantial homes, a school, a post office, and good roads. Its population was reported as 285 in 1990, but dropped to 265 in 2000.