The Strawberry Hill Races, formerly the Deep Run Races, organized and sponsored by the Deep Run Hunt Club, date back to November 30, 1895, when the first Deep Run Races were held at “Chantilly” on Board Street Road in Richmond. The first running of the “Deep Run Hunt Cup” took place the following year at the same location. The race meet changed locations during the ensuing years, being held for a time in Ginter Park and later at the current site of the Country Club of Virginia.

During World War I and for some time after, the Deep Run Races were not held. It was not until 1927 that the Deep Run Races were re-established and a steeplechase course was constructed at “Curles Neck” on the James River. It has been an annual event ever since.

In 1973, the Deep Run Hunt Club decided to discontinue its sponsorship of the race meet and the Atlantic Rural Exposition, now known as the State Fair of Virginia, Inc. took over this role, feeling the event compatible with its mission to support agriculture and with it, Virginia’s equine industry. At that time the race meet officially became the "Strawberry Hill Races," and was so named for the farm which originally occupied the location of the former Fairgrounds on Strawberry Hill.

In 2000, the Races were moved to Colonial Downs in New Kent County, Virginia’s first Thoroughbred race track. The facility features an outstanding turf course renowned in the racing world (a turf track is required for steeplechase racing) and excellent facilities and amenities. Its accessibility to central Virginia has made it an excellent venue for this event.

In 2011, for the first time at The Strawberry Hill Races, pari-mutuel wagering is available for LIVE RACES. Additionally wagering is offered for “simulcast” races, i.e. televised races that are taking place in real time at other locations around the country.

January, 2012, the sport of horse racing and the art of tailgating collide as Strawberry Hill Races moves to a new date and a new partnership with Colonial Downs Racetrack.