Horseracing was a popular amusement in Charles Town, West Virginia as early as 1786, and September 1808 issue of Farmer's Repository notified the public of three horseracing events the following month. Financed by private donations and club subscription fees, the sport flourished throughout the 19th century. The Shenandoah Valley Jockey Club, the first race track in the state, opened on 2 December 1933 in Charles Town shortly after West Virginia legalized racing and betting. The first two years proved financially unsuccessful. Convinced that promoting the race track during the winter season to residents in Washington and Baltimore would yield success, Albert J. Boyle (d. 1957) invested $160,000 in the venture, rechristening the organization as the Charles Town Jockey Club. His prediction proved correct, the business thrived, and Boyle remained a prominent figure in West Virginia racing.

Seeing the financial rewards possible, a newly formed group of investors purchased property across the road to construct a second race track. The group encountered resistance from churches opposed to gambling and the Charles Town Jockey Club, which wished to maintain its monopoly. After a contentious election, voters approved the new track by a narrow margin of 357 votes. Considerable litigation resulted in a decision by the West Virginia Supreme Court of Appeals that allowed construction to continue. The new track, known as Shenandoah Downs opened in 1959. For two decades, the tracks competed for prime racing dates from the West Virginia Racing Commission. The rivalry ended in 1972 when the Shenandoah Corporation, owner of Shenandoah Downs, purchased the Charles Town Race Track. From that point forward year-round racing continued at Charles Town Rack Track while the Shenandoah Downs operated as a training track.