The "oldest turf organization in America",[1] it was founded by a group of prominent locals, who included planter and politician Henry Clay, Jesse Bledsoe, Dr. Elisha Warfield, and Thomas F. Marshall.
On the property, the Association built a one-mile dirt racetrack with grandstand and stables to host Thoroughbred flat racing events.
Given the low economy, they had difficulty attracting horses for important events such as the 1896 Ashland Oaks, which the New York Times described as a farce after it drew only two entries.
On April 17, 1933, articles of incorporation were filed for the Keeneland Association; their new racecourse opened in 1935, located about six miles outside of Lexington.
Today city roads Versailles and Man O' War Boulevard intersect at one corner.