Although never incorporated, Fairplay was once a bustling agricultural community. In1897, Fairplay established itself with a gin, the Fairplay Post Office, a store, a school, and two churches, one of which was African American. By the early twentieth century, the boll weevil and the depression had taken its toll. Fairplay began to see a transition from cotton farming to more seasonal types of industry, such as orchards. Despite the “Dust Bowl Years,” the residents of Fairplay continued to build the community.

The 1939, Georgia DOT Map shows that Fairplay consisted of a store, orchards, various residential structures, Prospect Church and cemetery, Prospect School, Chestnut Grove African American Church and cemetery, and Chestnut Grove African American School. Many of these structures can still be seen in the Fairplay Community.