Kentucky Town was eighteen miles from Sherman in eastern Grayson County. Though the area was sparsely settled as early as 1837, a community did not begin to develop there until 1849, when the first substantial group of settlers, traveling in a wagon train from Kentucky, arrived. Others soon followed, and by the end of 1850 two stores and a mill, one of the first in Grayson County, had been established. On January 8, 1852, Dr. Josiah L. Heiston purchased land from Enoch Madison Jones (a settler who had arrived from Kentucky about 1848) and laid out a town, which he called Ann Eliza after his daughter. Because the town was populated primarily by settlers from Kentucky, it was soon referred to by such names as the Kentuckians' Town. By June 1854, when the first post office was established, the official designation was Kentucky Town. The first postmaster, Jacob Alfred Drye, also owned one of the first stores in Kentucky Town. The community, on stage and freight lines from Shreveport and Jefferson westward, grew rapidly. Charles DeMorse, editor of the Clarksville Standard, chronicled the speedy development of the town in an 1855 news report. According to DeMorse, only two residences had been in Kentucky Town when he had visited there three years earlier. In 1855, however, the town had two schools, a church, a lodge, a lawyer, and three doctors, and he credited the town with a precinct vote of 200. Kentucky Town continued to thrive throughout the 1850s. At one time as many as twenty businesses, including three saloons and two hotels, were located there. The Civil War years, however, brought a different type of excitement: William Clarke Quantrill and his guerillas frequented the area around Kentucky Town and wintered there at least once. The population of Kentucky Town began a steady decline during the 1870s, when the Texas and Pacific Railway passed to the north of the community, and the Missouri, Kansas and Texas line brought the Whitewright community into existence three miles to the east. By 1883 Jonathan Sewell's general store, which also housed the post office, was the sole business left in Kentucky Town. In 1924 the post office was discontinued and replaced by rural delivery from Whitewright. In 1988 scattered residences and the Kentucky Town Baptist Church, itself a Texas landmark, were the only vestiges of Kentucky Town. The population was twenty in 2000 and remained at that figure in 2010.
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