The first fair was October 3 – 5, 1887 in Hermosa. The second fair as held September 19-21, 1888. In addition to the crop exhibits it included shooting contests, horse races and a ball game.
The fair was held in Buffalo Gap 1889-1908 in the downtown area and the races were held on the streets.
From 1909-1945 the fair was held in Fairburn and Pringle.
In 1945 a group organized in Custer headed by County Agent, Mr. Simonson, planned and held the fair on August 27 & 28. The County Commissioners allowed $300 for prizes. The fair was at the old football field. No buildings were erected and the livestock were tied to the trees.
In 1945 through the efforts of the Hermosa Roping Club the County Fair was returned to Hermosa where it has remained. Harold Hasselstrom was the first president elected after this move.