In September 1945 six men discussed ways to raise money to build a hospital in Crawford. One of them suggested having a rodeo. The event was known as the Hospital Rally Day Rodeo. Organizers put some fence around the baseball field and put together several events. By 1947 the hospital project was nearly completed and the idea of an annual rodeo was met with enthusiasm from the community. The date was changed to the 4th of July. Lights in the arena were not introduced until July 1949 when the rodeo association and the Crawford baseball association (who at the time shared the arena) made a joint effort to have lighting installed.
In 1946, The rodeo was sanctioned by the Rodeo Cowboys Association and was under the sponsorship of the Northwest Cowboy's Association until 1949. The rodeo board, community and cowboys of the area decided they preferred the "Professional Cowboy" designation. Crawford's rodeo was one of 500 Rodeo Cowboy Association approved rodeos during the 1950's.
In 1981, the rodeo, which had been known by a variety of names including the "Crawford Fair and Rodeo Association", was officially renamed to "The Old West Trail Rodeo".
In May 1991 a flood roared through Crawford. The rodeo grounds and adjacent City Park were under water. Fences were twisted and smashed against the bucking chutes. Rain from the hills filled the arena with 3 feet of debris and mud. The concession stand was shoved off its foundation and the Park Pavilion that had hosted numerous rodeo dances was damaged beyond repair. That year the rodeo was held at the arena at Fort Robinson. Determination and love of rodeo resulted in the arena being rebuilt. The Rodeo returned to its home in 1992.
Today, The Old West Trail Rodeo is sanctioned by the Professional Rodeo Cowboys Association (PRCA). Performances are on the 3rd and 4th of July each year in the Crawford Rodeo Arena.