Coordinates: 38°02′47″N 84°28′48″W / 38.04639°N 84.48000°W
The Kentucky Association (also known as the Kentucky Racing Association) was formed on July 23, 1826 to promote the breeding and racing of Thoroughbred horses in the Bluegrass region of Kentucky. The "oldest turf organization in America", 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. Between 1828 and 1834, the Association acquired 65 acres of land in an area of the city of Lexington, Kentucky that today is the east end of 5th Street at Race Street. On the property, the Association built a one-mile dirt racetrack with grandstand and stables to host Thoroughbred flat racing events.
After more than six decades of success, financial problems led to the track being sold in 1890 to a group of investors. The economic depression following the Panic of 1893 was a serious blow, and financial difficulties plagued the new owners. 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. Facing imminent foreclosure, on March 18, 1897 the track was put up for sale. The status of the track remained in limbo for four years until Charles Green of St. Louis, Missouri, who had been a Trustee for the stockholders, purchased the track in 1901 for $1 plus other considerations.