Before Stonewall was a town, it was primarily the Chickasaw tribes land. Robert L. Cochran was a Georgia man who settled Stonewall first by opening up a trading post on the original site of Stonewall. The site was declared Pontotoc, which would become the county name in the present. Along with the settling of Cochran's store a post office opened there in 1858. The settlement was then named Stonewall in honor of confederate war general Stonewall Jackson. By the late 1800s, Stonewall had increased in population and had multiple businesses open such as a cotton gin, good stores, a hotel, and stagecoach station.