Hills Prairie, four miles south of Bastrop in central Bastrop County, had its origins when Elisha Barton and Edward Jenkins settled in the area about 1830. In spring 1833 John Gilmer McGehee explored the prairie, and in 1835 he returned with a colony of 140 people from Alabama and Georgia. Their settlement near the Jenkins homestead was called Hill's Prairie after Abram Wiley (Wylie) Hill, a settler who bought 2,220 acres from Edward Jenkins's widow, Sarah, and established his home on the prairie. The community built a private school, and Methodist religious services were conducted in the Hill and McGehee homes. In 1843 Wiley Hill built a cotton gin. In 1877 a post office was established at Hills Prairie with John McDonald as postmaster. The community's population in 1884 was thirty. Four years later the post office was renamed McDonald's Store, but the name was changed back after two years, when Sarah Hill became postmaster. With the extension of the Missouri, Kansas and Texas Railroad through Bastrop County in the 1880s, Hills Prairie became a railroad station. In 1896 the community had fifty residents, a drugstore, a general store, and a swine dealer. By 1914 the population had risen to seventy-five, and the site had a combination general store and cotton gin, as well as second cotton gin. By 1925 the population had fallen to six. The Hills Prairie school was abandoned in 1928, and the post office was discontinued in 1930. In the late 1930s the population rose to twenty-five and in the late 1940s to fifty. After reaching a peak of sixty-two in the late 1960s, Hills Prairie population estimates stabilized at thirty-five, where they remained through 1990. By 2000, however, the population had grown to fifty.
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