Hillhead is located at the head of one of the many hills in the Coteau des Prairies Hills.
The town was established in 1915 when the branch line of the railroad from Veblen to Grenville was built. A Post Office was opened in 1916 unter the name Airmont. But the name apparently became confused with Fairmont, ND, and the name was changed to Hilltop. Then when it was determined there was another Hilltop in western South Dakota. The town's name was changed once again to Hillhead in 1917.
The town grew quite rapidly and supplied area farmers and ranchers with a variety of supplies and services.
Hillhead reached its population peak from 1920-1927.
