Grove Hill, first inhabited by Choctaw Indians, was settled by pioneers in the early 1800s. The settlement was called Magoffin's Store after James Magoffin whose shop, two miles from the present courthouse, opened in 1815. Grove Hill has also been known as Smithville and Macon. There was little activity in Grove Hill prior to 1832 when the county seat moved from Clarksville to its present site, and a one-story frame courthouse was constructed. During the 1830s, Grove Hill was one of the principle towns in the county. One of the earliest businesses in the county seat was a hotel kept by Tom Brown, a free man of color. The oldest continually operating business in Clarke County, the newspaper called the Clarke County Democrat, began in Grove Hill in 1856. Both business were located on the north side of Main Street in front of the Courthouse.
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The first school, Macon Male and Female Academy, opened in September 1846. In 1909, Clarke County High School was established in a two-story brick building located on the school's present site.
A sad episode in the town's history occurred in the summer of 1853 when a terrible Yellow Fever epidemic swept through the area. Many of those who died are buried in a cemetery near Church Hill Street and in Spinks Cemetery on Asbury Road. A second courthouse structure, an attractive two-story brick building, constructed in 1899, was razed in 1955 to make way for the present courthouse building which was completed the same year.