In the era when life still moved slowly enough for daydreams, and neighbors visited each other on front porches, cowboys competed in the first Sisters Rodeo. These cowboys, both amateurs and professionals, wore cloth squares hand painted with numbers pinned to their backs and waited for their events. Because the small-town rodeo offered purses of $500, equal to Pendleton and Cheyenne, the cowboys tagged Sisters Rodeo “The Biggest Little Show in the World.” The year was 1940.

Local couples had pooled $10,000 to produce the rodeo east of town on land next to the site that became Sisters Airport. Two years later, they purchased land on the west end of town and held rodeos there for the next thirty-four years. The events included bull and bronc riding, calf roping, bulldogging, wild cow milking and wild horse races.