Cunningham is home to Montgomery Central High School and cradles the split of state Highway 48/13 about halfway between Clarksville and the Dickson County line. The community used to be known as "Lone Oak," a moniker that originated because children once played baseball in a field off Highway 13 where a lone oak tree stood. The name Lone Oak has survived on signs identifying roads such as Lone Oak Lane and Lone Oak Station Road. Cunningham also hosts the annual political stomping ground, the Lone Oak Picnic.
Some Cunningham residents like to call the community by its nickname — Boogersville.
The community's official name eventually changed from Lone Oak to Cunningham, after an influential resident.
Cunningham's staple once was farming, but the community has grown into a residential neighborhood. A couple of country stores, a post office and a day care accompany the high school.