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While Ashland had been home to some famous human beings (Henry Clay preeminent), the estate was for about a century the birthplace, home, and burial ground for some very celebrated horses.
Henry Clay began racing thoroughbreds for pleasure in 1809. He was involved with the Lexington Jockey Club until 1823 and sometimes held private races on one of the tracks he created at Ashland. As former Ashland curator Jeff Meyer observed, “What began as a hobby for a young lawyer and aspiring politician had turned into more than a century of success for Henry Clay’s family.” The Louisville Courier-Journal observed in 1883: “All of the Clays … have been great lovers and admirers of the thoroughbred horse and almost from the first settlement of Ashland until the present time the tread of the high-mettled racer or the footsteps of the trotter has almost continually pressed the soil at Ashland.”
This equine empire really began in 1830 when Henry Clay established his breeding operation, the Ashland Thoroughbred Stock Farm. He would become one of the leading horsemen of the era. In 1845, Ashland Stud’s success was assured with the gifts to Clay of three extraordinary horses: Margaret Wood, Magnolia, and Yorkshire. For more on Clay’s horses, see Ashland’s website.
In 1842, Clay handed over the day-to-day operations of Ashland Stud to his youngest son, twenty-one-year-old John Morrison Clay, who proved to be highly adept. When Henry Clay died in 1852, John continued to successfully manage the breeding operation, now located on the adjoining property his father had left to him, which he named Ashland Stud on the Tates Creek Pike (or Ashland-on-Tates-Creek). During the Civil War, Ashland’s fine horses would prove a desirable prize for John Hunt Morgan who proceeded to steal $25,000 worth of John’s stock (forcing John to pay ransom for his horses). John would breed Ashland’s first Kentucky Derby winner: Day Star (1878).
After John died in 1887, his widow Josephine continued to ably handle Ashland Stud, doing business with men and breaking down barriers for women, while proceeding to foal Ashland’s second Kentucky Derby winner, Riley (1890).
John Clay was not the only son to perpetuate the breeding of star horses at Ashland. James owned and occupied the main part of the estate and went on to breed harness horses – standardbreds – at Ashland. He was a pioneer in introducing and popularizing harness racing and the standardbred in the Bluegrass. James laid out one of the racetracks at Ashland, a one-mile trotting track behind the mansion near the Richmond Pike.
After Kentucky University vacated Ashland in 1879, the estate was for a few years leased to private tenants who continued to utilize it as a horse farm. First, Wood Stringfield established his racing stable and used James’s track at Ashland, then A. Smith McMann brought his trotters to Ashland.
But the Clay family returned to Ashland in 1882 with Henry Clay, Jr.’s daughter Anne and her husband Major Henry Clay McDowell took on the estate. McDowell had been a Civil War veteran with business interests in real estate, railroads, mining, and land development. But he became most known for breeding trotting horses at the second Ashland Stud (John and Josephine’s adjacent farm would be distinguished by “On-Tates-Creek”).
McDowell converted the large, brick Kentucky University Mechanical Building by adding box-stalls and a small track inside for his horses. He most likely added another mile track on the estate, as well. His most famous horse, Dictator, foaled in 1863, and soon to become the most famous stallion in the country, died at Ashland in 1893.
Major McDowell handed the operations of Ashland Stud over to his son Thomas Clay McDowell, who soon went back to breeding thoroughbreds. Thomas bred, owned, and trained Alan-A-Dale, the last Kentucky Derby winner produced at Ashland. Jimmy Winkfield, the final African-American jockey to win the Derby, rode Alan-A-Dale to victory in 1902.
Both Alan-A-Dale and Dictator were buried at Ashland “just to the right of the broodmare barn entrance” (exact locations unknown).
Thomas eventually moved his breeding operation to Woodford County when property values around Ashland skyrocketed, while Josephine Clay had shuttered her stud farm years before. By the 1920s, Ashland Stud was no more.
 Meyer, Jeff. “Henry Clay’s Legacy to Horse Racing.” In exhibition catalog for the Kentucky Horse Park’s 2005 exhibition, “Kentucky Bloodlines: The Legacy of Henry Clay.”