The first Ogle County Fair was held in October of 1853 on the lawn of the Ogle County Court House. In the early years, it was held a several places and on one occasion, in Byron.
In 1856 a group of citizens purchased 10 acres of land in the north section of Oregon along Illinois Route #2. An additional 10 acres was purchase in 1858 followed by the acquisition of 6 acres from Mr. E.S. Potter in 1901. Ten more acres were latter purchased from the estate of James H. Cartwright. The grandstand was constructed in 1925 followed by the horse barn in 1927. The fair encompassed approximately 40 acres by 1968.
Moving forward to more current times the Ogle County Fair decided to discontinue operation and the last fair at the fairgrounds on the north edge if Oregon was 1991. The city of Rockford invented a festival call “On the Waterfront” and the attendance had dropped extremely and was no longer viable. Since the Ogle County Fairground was privately owned it was put up for sale. Twenty three acres were purchased by Grant and Janice Landis of Oregon and the remainder by the Oregon Park District. The Ogle County Fair needed to find a new home.
Since the fairgrounds was used for the Ogle County 4-H show each year a group of 4-H parents and concerned citizens was formed to find a new fairgrounds. This was a daunting task, but was achieved in 1993. There was a minimal fair held by the 4-H in 1992 at St. Mary Learning Center located West of Oregon, just off of Illinois Route #64.
With the help of the Ogle County Farm Bureau 20 acres of land was purchased from the Estate of Marian and Homer St. Clair in April 1993. This property became the home of the Current Ogle County Fair. Since the buildings on the old fairground were not in the best of shape they were donated to the New Ogle County Fair and were razed and moved by a large group of volunteers to the new site. In early 1993 a fair board was created and the new organization was chartered as a 501-C-3 Not for Profit Organization.
It was determined very quickly that the 20 acre purchase would not be large enough to provide for the needs of the fairgrounds. The Ogle County Farm Bureau then purchased the remaining 18.3 acres in May of 1994. This parcel was quickly turned into the track and grandstand area of the fair grounds.