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The very first Garrett County Fair was held in 1917 in the Naylor Building on Third Street in Oakland, and the lot between that building and Center Street. Later, sheds were constructed near Center Street on the Sweeney lot to house part of the exhibits, and successful fairs were held at this location until the early twenties.
As interest in the Fair increased, it became necessary to have more space, so the Bradley property west of Oakland was purchased. Some of the exhibits were housed in the Bradley house. A shed was erected for the livestock and poultry entries. The last of the fairs held at the Bradley farm location was in 1931. Most of the earlier Garrett County fairs were held in late September, because more farm products were available for showing at that time of the year. However, many people who had experience with these fairs said that attendance and general support were in direct relation to the weather, and the weather here in late September is often less than ideal for going to the fair.
Several years of bad weather during fair week resulted in financial losses and the Fifteenth Annual Garrett County Fair, September 15, 16, 17 and 18, 1932, was the last until 1957.
Meetings were held early in 1954 to again organize a Garrett County Fair.
H.G. Gortner, Allen S. Paugh, Sr. Walter DeBerry, Baity Ridder, and then County Extension Agent, John Carter, were among those instrumental in working out details for the first Garrett County Agriculture Fair, Inc. held August 13-17, 1957, on the property of Charles H. Bowman, near Deep Creek, McHenry, Maryland, where the present Fair is held. Officers elected were H.G. Gortner, President; John J. Brenneman, Vice President; Charles A. Wilt, Secretary; Allen S. Paugh, Sr., Treasurer; and Claude W. Wagner, Sr., Manager. The Board of Directors was composed of sixteen men and four women to serve for four-year terms.
The property had one Quonset hut for the first fair. Other tents and temporary buildings were used to house the exhibits and animals. Many improvements have been made to the fairgrounds through the years. Today Garrett County Fair stands as one of the true remaining agriculturally based fairs in the state.