IN 1793, A VIRGINIAN BY THE NAME OF JOHN BRECKINRIDGE bought 2,467 acres of prime Kentucky farmland. He named the farm, which would later become known as Castleton, “Cabell’s Dale.” Breckinridge was a dedicated thoroughbred breeder who would himself go on to become a United States Senator and to serve as Attorney General in the cabinet of President Thomas Jefferson.

Upon Mr. Breckinridge’s death in 1806, the property was inherited by his daughter, who married David Castleman in 1816. In 1840, Castleman built the Greek revival mansion that is still a landmark of the farm, and he named the farm “Castleton.”

Like the Breckinridges, the Castlemans were breeders of horses. The Castleman’s initially bred thoroughbreds, but later became involved with saddlebreds and trotters –– introducing the farm to a breed that would make it famous in years to come.

The ownership of Castleton passed through a number of hands in the late 1800’s before it was acquired by Wall Street investor James R. Keene. Keene transformed Castleton into probably the greatest thoroughbred farm in the United States at the time –– with thoroughbreds such as DOMINO, SYSONBY, SPENDTHRIFT, PETER PAN, KINGSTON, SWEEP, BALLOT, BLACK TONEY, BEN BRUSH (1896 Kentucky Derby winner) , and COLIN. In 1908, London Sportsman Magazine declared that Keene possessed, “the greatest lot of race horses ever owned by one man.”

Keene exited the business as thoroughbred racing fell on hard times on the ‘20s. For it’s next owner, Castleton would again become a trotting farm –– the new owner was David Look, another New Yorker. Look would go on to have significant success with names such as SPENCER, and SPENCER SCOTT (1944 world champion trotting stallion).

During the Depression, Look encountered financial difficulties and sold the farm in 1945. In the decades that followed, Castleton was rebuilt and returned to glory under the ownership of Fredrick and Frances Dodge Van Lennep.

The Van Lenneps invested heavily in both their show horse empire and their standardbred operation, and Castleton climbed to the top in both disciplines.

At the head of the show horse class was WING COMMANDER, the six-time World Grand Champion, hailed as the greatest fivegaited show horse that ever lived. The show division was disbanded after the death of Frances Van Lennep in 1971.

In late 2001, Castleton changed hands again when Dr. Tony Ryan purchased the farm from the Van Lennep Trust. The farm was again to return to its thoroughbred roots. Ryan, an Irish businessman, made his fortune in the aviation industry.

And, on February 10, 2004, the breeding shed at Castleton –– now renamed Castleton Lyons opened its doors. Castleton Lyons once more finds itself on the map in the thoroughbred breeding industry –– and things are only starting.