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.
The very first transportation routes in the Alabama Territory and the newly formed Henry County, mainly followed old Indian paths. Early settlers entering the new lands, now Henry County, stayed close to Ft. Gaines, Georgia for protection from the Indians. There were no roads on which to venture into the unsettled wilderness. Among the early settlers that were settling just across the river in the first town in Henry County, Franklin, were Daniel Jackson and Matthew Jackson, brothers seeking a new life in a new land circa 1820. They had a third brother whose name is not known. It is said that brother lived to be 114 years old. Daniel and Matthew Jackson cut the very first road in Henry County and Southeast Alabama in 1820.