Town of Leonardtown
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Leonardtown is one of the oldest communities in the United States. Records dating back to 1654 indicate that the county court was held here in private homes; the town became the official county seat in 1708. Vintage photos throughout the decades depict horses as an integral part of daily life.

Horses worked the fields, pulling plows and other farm equipment. Horse-drawn carriages carried citizens to church, and the blacksmith’s forge was a fixture in town.

Stud-Horse Day in Leonardtown. The first Tuesday after the third Monday in March was the day big cases were tried in town. But more importantly, it was the day horse owners came from all over the county to hawk stud services. Known locally as Stud-Horse Day, it was marked by a carnival atmosphere complete with drummers, agents, gamblers and traders of every description who had flocked to the county seat for a chance to turn a fast dollar. Beribboned stallions pranced through the streets drawing road carts. Hundreds of buggies, carriages, sulkies, wagons, carts and nondescript vehicles overflowed the town. Farm machinery was displayed, and methods and prices discussed.[Excerpted from an editorial from the Enterprise, March 18, 1954] Click here to see a collection of vintage stud flyers.

Leonardtown Thoroughbred race track. “The sport of kings also has a long history in Leonardtown. The first racetrack was where the current Governmental Center is located on the east side of Washington Street (SJW note: now Hollywood Road). This was also the site of Thronley, the estate of William Alexander Loker, and later an important school site. The second racetrack was located across Washington Street (SJW note: now Hollywood Road) and ran from about Doctor’s Crossing Drive towards Mile Post Lane. The area became known as Racetrack Farm. A Jockey Club began in May, 1863. Benjamin G. Harris, George C. Morgan, and John H. Tucker represented the Leonardtown district in this county-wide club. Races continued at that site until 1910.” [Excerpted from Aleck Loker’s “A Most Convenient Place; Leonardtown, Maryland 1650-1950”]

Clark’s Rest Farm. “In 1968 a new era of activity commenced on “Clark’s Rest” when George Clark began breeding and raising thoroughbred race horses. Stables were built for the horses and a successful breeding, training and racing career ensued. Townspeople typically commented how they marveled at seeing the horses and yearlings running and playing in the open fields. Many may still recall such favorites as Miss Leonardtown, Leonardtown Queen, Fun-N-Fancy and Son of Fancy. This venture reached its peak when Son of Fancy won the Senatorial Sweepstakes at Pimlico in 1973. Horses continued to graze the pastures of “Clark’s Rest” until George Clark’s death in 2003.” [Excerpted from Leonardtown Beacon, Spring 2013 Issue]

Much of the information for this listing was excerpted from documents provided by the St. Mary’s County Historical Society. Top photo: Parishioners arriving by horse and buggy to Church of Our Lady in Medley’s Neck. Photo courtesy of St. Mary’s County Historical Society.

Photos courtesy of Saint Mary’s County Historical Society unless otherwise noted.