The first rally was held on 14 August 1938, by the "Jackpine Gypsies" motorcycle club,[1] who still own and operate the tracks, hillclimb, and field areas where the rally is centered. The first event was called the "Black Hills Classic" and consisted of a single race with nine participants and a small audience. The founder is generally considered to be Clarence "Pappy" Hoel. He purchased an Indian Motorcycle franchise in Sturgis in 1936 and formed the "Jackpine Gypsies" that same year.

The focus of a motorcycle rally was originally racing and stunts. In 1961, the rally was expanded to include the Hillclimb and Motocross races. This could include half-mile track racing (the first year in Sturgis, there were 19 participants), intentional board wall crashes, ramp jumps and head-on collisions with automobiles.

The Sturgis Rally has been held every year, with exceptions during World War II. For instance, in 1942, the event was not held due to gasoline rationing.

This rally is not for the weak of heart or the younger children. Drinking in public and public nudity are occasional problems for the local police.