First held in 1895, the charter run was known as “Deep Run Hunt Cup,” and was held on Broad Street Road. Subsequent runs were held at Ginter Park and later, on the grounds of today’s Country Club of Virginia.

During World War I, the Cup went on hiatus and resumed in 1927. It was also suspended during World War II. Today, thousands eagerly watch the races to see who comes away with part of the purses totaling nearly $70,000.

The races are named after the farm, Strawberry Hill, where the races were held on Laburnum Avenue from the 70s to the late 90s. The Strawberry Hill Races moved to Colonial Downs in New Kent County in 2000 which features grandstand seating and two fancy cocktail lounges: the Jockey Club and the Turf Club.