Headland was officially established on October 10, 1871, when the U. S. Post Office was opened at “Headland, Alabama”. However, Headland was settled before this time. A settlement was already at the location where the Eufaula-Marianna mail route crossed the Columbia-Newton Road just after the Civil War. The “Church of Christ at Bethlehem” was formed here circa July 1, 1868. This church was the start of the First Baptist Church of Headland. This church was located about where the Quince Hollon house later stood on Cleveland Street. Also, another settlement had been started about a mile east of present Headland by a Johnson family and was called “Johnsontown”. The family of Mr. Thomas F. Espy later lived on this property. He was the grandfather of Major W. Espy. Also, the Piney Grove Primitive Baptist Church had been organized in 1849 northwest of present Headland.