The Fairgrounds were established in 1903. Originally it was only a race track and some grand stands that were built on the grounds where the current Fairgrounds are located. In 1904, the first Central Oregon Fair was held primarily comprised of an annual horse race and some small exhibits. In 1915, the Fair sold half of the ground and the track was reduced to the current 1/2 mile oval. J.B. Shipp and Gardner Perry owned and operated the grounds until 1935 when Perry sold to M.D. Spreckles, Jr. of San Francisco. In 1936, Harry Walters bought it and in 1940 he sold to Robert Lister of Paulina, who in turn sold the grounds to Warren Raymond. In 1945, when the Crooked River Roundup and Fair Association were formed they purchased the ground from Mr. Raymond.
In 1914, the 4-H Program was established in Crook County. In 1917, The Fair name was changed to the Oregon Interstate State Fair. In 1927, the Fair name was changed a final time to The Crook County Fair. In 1945, The Crooked River Roundup and Fair Association were formed and the first Roundup Rodeo was held. On September 2 and 3, 1945 the First Crooked River Roundup and 4-H Club fair was held.
In 1946, the fairgrounds had a major face-lift. New bucking chutes, new fences and a new foundation for the grandstand were added. A city block was dedicated for the 4-H Club Fair and 30 stalls were built for stock. All of the buildings were repainted white with green roofs. A sawdust arena was built for showing the stock. In 1948, lights were installed in the arena and the school district began holding night football games in the arena.
In 1954, it was decided that the Fair and the Rodeo should separate. The Fair board and the Roundup signed a 50- year lease for the 4-H corner of the “Roundup Grounds”. The Roundup and the School Board entered into an official agreement for the use of the grounds for football games.
In 1972, the Roundup made a bold move. At this time laws were being changed in Salem to force non-profit organizations to pay property taxes on the property they owned. The Roundup board was facing certain bankruptcy unless something was done. Their cash reserves were nil. The idea came up to deed the Roundup grounds over to Crook County at no cost. In exchange, the Roundup would get five years of free rent and the community would get the grounds to develop and operate on a year round basis. Crook County also had access to Federal and State grants and revenue sharing programs to help upgrade facilities. It was the only viable choice the Roundup Directors and Stockholders had at the time.
The year 1979 saw an extraordinary set of circumstances take place. The County had acquired a grant to build a first class indoor arena on the grounds. This would allow for more indoor events and full, year round use of the fairgrounds. The original plan was to build an indoor arena. While the design process was taking place, problems were found with the existing wooden grandstand. A decision was made by the County to tear down the wooden grandstand. The indoor arena project would be scaled back, and the money saved would be used to build the new grandstand. Crook County, the Fair Board, and the Roundup worked together to build a new jockey's room, paddock, and pari-mutuel building. Food booths needed to be moved to fit into the new layout. The grandstand was repositioned in comparison to the racetrack, so about half of the racetrack had to be rebuilt. Lighting was reconfigured to accommodate these changes.
In 1989, the Roundup purchased 40 portable stalls which were located at the Jefferson County Fairgrounds and moved them to Prineville. This made it possible to stall all of the race horses in actual stalls and it also helped to make the Fairgrounds the "Horse Capitol" of Central Oregon. A few years later in 1991, major renovations and work at the Fairgrounds were completed. Through connections with other race tracks in Oregon, the Roundup was able to have lights donated to relight the race track providing a safer racing environment and enhanced viewing for spectators. The box seats were also re-built through hard work and local donations.
In 1995, the Fair Board elected to move the Fair date from the second weekend in August to the third weekend in July. The July dates remained in place through 2006. Another schedule change came in 2007, when the Fair Board moved the Fair dates back to the second weekend in August.
In 1999, funding was secured through County funds paired with a state grant to construct a new office, maintenance shop, and a more attractive entryway.
Fairs in Oregon
Bicentennial of Fairs in Oregon-2014 marked the 203rd anniversary of Oregon fairs. Centennial of 4-H- 2014 also marks the 103rd anniversary of the 4-H. The 4-H movement began around the start of the 20th century and revolutionized how science was taught outside the classroom – through practical, hands-on programs and experiences. 4-H was also one of the first organizations in America that taught young people leadership skills and how to positively impact their communities.