Headland was not established until after the Civil War. The area was covered in standing ponds and virgin long straw pine trees. The countryside was sparsely settled. New settlers began arriving in the area seeking a new life after the war. They began clearing the land for cultivation. Headland began near the crossroads of the Eufaula, Alabama to Marianna, Florida mail road and the Newton, Alabama to Columbia, Alabama road. William Whitehead and wife, Matilda, claimed 160 acres near the crossroads. They were among the few charter members to establish the Church of Christ at Bethlehem on their 160 acres. This church grew into the present First Baptist Church of Headland. The oldest entity in Headland today is the Piney Grove Primitive Baptist Church established in 1849 near the three cornered pond in the West side of town.
A Confederate veteran, James Joshua Head, purchased the land claim from William Whitehead in 1869 and then received a patent or first deed from the Federal Land Office. J.J. Head laid out a public square in 1871 for a proposed town and country branch court house. He first platted the south and west sides of the public square and built a storehouse and began selling business and residential lots. He constructed his house beyond the northeast corner of the square. The little place was being called "Head's Land" by locals. On October 10, 1871 a U.S. Post Office opened at "Headland, Alabama" and the town was officially established. Headland had only several dozen citizens. J.J. Head sold his mostly undeveloped village to Hosey C. Powell in 1879 and became a doctor, opening his practice in Headland. Headland's population was still minuscule with only about 100 people, even though the countryside was increasing as new pioneers were moving into the area. An attempt to incorporate the village failed for lack of people in 1879. A young doctor from Abbeville, Dr. Wyatt S. Oates, had opened his practice in Headland in 1875. He soon closed his medical practice to manage his ever enlarging real estate empire. Dr. W.S. Oates purchased the mostly unsold portion of the Town of Headland from H.C. Powell in 1880. Dr. Oates then became the town's promoter, builder and developer and was called the "Father of Headland." Dr. J.J. Head moved from Headland in 1883 to Tampa, Florida where he remained until his death in 1927.
Headland incorporated in 1884 with barely enough voters to sign the petition. The population was around 150 with only 32 votes cast in the incorporation election. The railroad came through town in 1893 while the population had not yet reached 500. By 1900, Headland had 602 people. Being surrounded by rich farm lands, Headland's growing agricultural economy boomed. During the first quarter of the 1900's, Headland witnessed an economic explosion with the first new banks, steam cotton gin houses, cotton oil mills, lumber and turpentine operations and built the largest cotton oil mill in Alabama by 1912. Cotton was king. Headland was attracting new residents and businessmen, new hotels, new homes, new churches, new schools; and by 1911, Headland had the most automobiles registered in Henry county, along with the county's first hospital and the new two story brick Henry County High School. Headland's Public Square became surrounded by new brick storehouses for sale or for rent. The population reached 1,500 by 1915. The entrance of the dreaded cotton boll weevil spurred a new crop of peanut farming to emerge on local farms by 1916. By 1927, Headland's population reached 2,000. Alabama's first new agricultural experiment sub-station farm under the present system was built in Headland in 1928. The quality of life was expanding. The Great Economic Depression & Panic of the 1930's slowed the town's growth for the next 50 years; however, the town began to grow slowly after WWII. The population was 2,052 in 1940; 2,091 in 1950 and 3,327 by 1980. By 2000, the population was around 4,000.
Henry County became the No. 1 peanut county in Alabama in the 1950's, and Headland is still a peanut and cotton town. A new federal four-lane highway was built near the town in the 1960's. By the early 2000's, Headland once again experienced a growth period, becoming the fastest growing town in Alabama; and excelling as the largest town in Henry County with 5 banks and a credit union. The city limits have recently expanded; new grants have been obtained for improving the Public Square and the downtown area, and upgrading the infrastructure systems, and for preserving the history of the town. Headland is greatly expanding her social, educational, religious, residential, recreational and business facilities for present and future needs. The old mottos in promoting Headland during the 19th and 20th centuries remain true today; Headland is the Gem of the Wiregrass and Headland is a Good Place to Live. The City of Headland is forging ahead into the 21st Century with a vision of hope and prosperity for the well being of her people. Headland and Henry County have so much History; and so much Future!