Headland is the largest city in Henry County, Alabama, United States.

The Headland Public Square was laid off in 1871 by Head with a vision for a branch courthouse.

Headland lost that distinction to Abbeville again in 1970, but regained it in 1980 and has since solidified its hold.

U.S. Route 431, a four-lane highway, passes through the east side of Headland, leading south 10 miles (16 km) to the center of Dothan and north 18 miles (29 km) to Abbeville.

Alabama State Route 134 runs through the center of Headland, leading east 16 miles (26 km) to Columbia next to the Georgia line, and west 10 miles (16 km) to Midland City.

25.3% of all households were made up of individuals, and 12.3% had someone living alone who was 65 years of age or older.

As of the 2020 United States census, there were 4,973 people, 1,583 households, and 1,131 families residing in the city.

Headland is a part of the Henry County Public Schools system.

Headland was also the home to the 2016 Dixie Youth Baseball World Champions.