Headland is the largest city in Henry County, Alabama, United States. It is part of the Dothan, Alabama's metropolitan area. At the 2010 census, the population was 4,510 up from 3,523 at the 2000 census. Ray Marler is the current mayor.
James Joshua Head (1839–1927) founded Headland in 1871 as "Head's Land". He patented land, plotted the town and built his home. The post office opened, as "Headland", on October 10, 1871.
The Headland Public Square was laid off in 1871 by J.J. Head with a vision for a branch courthouse. Henry County voters decided in the 1879 and 1885 courthouse site elections not to locate a courthouse on the public square. Henry has been Alabama's only county with three courthouses at the same time.