- Welcome to Headland, Alabama Gem of the Wiregrass Find Out More About ... Current Events Chamber of Commerce Community Information Economic Development Other Links The Heritage of Headland Headland was originally listed with the U.S. Land Office in Montgomery as Township #4 Range No. 27B, by Dr. Joshua J. Head in 1865. The settlement's registration included about 160 acres in the southern part ...www.headlandal.com