James Joshua Head (1839-1927) founded Headland in 1871 as Head’s Land, patented land, platted the town, and built his home there. The Post Office opened as Headland on October 10, 1871. J. J. Head sold Headland to Hosey C. Powell in 1879, who sold it to Dr. Wyatt S. Oates in 1880. Head moved to Tampa, Florida, in 1883 and later established Lake Magdalene. Headland incorporated in 1884 with 26 white and 4 black petitioners, and the railroad and depot were built in 1893. By 2000, Headland had grown into Henry County’s largest city. The public square was laid off in 1871 by J. J. Head with a vision for a branch court house, but Henry County voters decided in the 1879 and 1885 court house site elections not to locate a court house there. Henry County was Alabama’s only county with three court houses at the same time. In 1908, the Alabama Supreme Court ruled that the town of Headland held title to the square rather than Dr. W. S. Oates, who had claimed title when he purchased the town in 1880. Dr. Oates was instrumental in Headland’s development. The first public statue in Henry County was erected on the square in 1926, and the square was paved in 1935.