According to a history published by the Association, the Litchfield Horse Show was one of the oldest in the country. It had its inception in a fair held under the auspices of the Litchfield County Agricultural Society first held in 1839. The fair continued through the 1800s during which time the horse show was one of a number of events. The first distinct horse show was held in 1912 at Kilravock Farm in Litchfield and had eight classes. Annual horse shows, some or all of which were held under the auspices of the Litchfield Lawn Club, continued through 1917. World War I and a lack of interest brought an end to the shows until August, 1928, when the event reappeared on the grounds of Mr. and Mrs. E. H. Outerbridge. In the same month, the Litchfield Horse Show Association was formed, with by-laws, membership, and dues. The first officers were Alain White, president; John C. Barnard, vice-president; Hobart Guion, secretary; and George Guion, treasurer. The new association sponsored an annual horse show in August on the grounds of a private estate in Litchfield, with a portion of the proceeds from the event going to a local charitable organization, such as the Connecticut Junior Republic or the Litchfield Public Health Nursing Assn. By 1932, the association had become a member of the American Horse Shows Associations, Inc., adopting its rules. In 1940, the Litchfield association located an 1839 newspaper article describing the original agricultural fair and adopted that as an anniversary date; its 1940 program carried the legend "Celebrating the 101st anniversary of first recorded horse show in Litchfield." The phrase would later be shortened, giving rise to the statement that the Litchfield Horse Show was one of the oldest horse shows in the United States. The show was not held during World War II. In the years that followed, the number of classes substantially increased, and both entrants and spectators came from beyond Connecticut. Publications such as The New York Times, Sports Illustrated, and The New Yorker listed the shows on their calendars. In 1952, the association inaugurated a Horse Show Ball, further increasing the event's prominence on the Litchfield social scene. The final Litchfield Horse Show was held in 1975. According to then-Assn. Pres. Michael Ducey, the reasons for the demise were that the event had become too large to be managed by volunteers, costs had increased, and local riders were no longer able to compete with the large number of out-of-town competitors

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