The tradition of racing horses in Virginia began after the first horses were brought to its shores in 1609. The colonists in Virginia continued the English gambling tradition of betting on horses. The Virginia Company of London which financed the colonization of Virginia until 1624 had to rely on lotteries to survive at one point. After Charles II was restored to the throne in 1660, English society replaced the current Puritanism with widespread gambling.

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Horse racing then became identified as the “Sport of Kings” because only the very wealthy could afford to import horses for breeding or to maintain a horse for no productive use other than racing. Everyone could bet, but the gentry in colonial Virginia may have been the only class able to afford owning a race horse. In 1674, the York County court imposed a fine on a tailor who had the nerve to race his horse since it was “contrary to Law for a Labourer to make a race, it being a sport only for Gentlemen.”

Many races were 1/4-mile straight dashes held on Saturday afternoons on open fields and straight sections of road, or “best-of-three” challenges where horses would run separate races up to 3-4 miles in one day. The steeplechase race became the formal race that occurred on open courses through the Virginia countryside. These races were cross-country contests where start/finish lines were marked by steeples of churches, between drivers with wagons on roads and on circular racecourses.

The first racetrack in the colonies was built at Hempstead Plain on Long Island, NY and the first in Virginia was a 1-mile oval operating by 1739 at Williamsburg. Horses circled the track several times to complete one race, compared to today’s races of one-and-a-quarter miles (one-and-a-half miles for the Belmont Stakes).

In 1752, William Byrd III claimed he had the fastest horse in the colonies. That challenge was bold enough for a member of the Maryland aristocracy to walk his horse 150 miles to Anderson’s Race Ground in Gloucester for a match race. In the first Maryland-Virginia contest, the Maryland stallion beat Byrd’s horse plus two other Virginia stallions owned by John Tayloe. Byrd went on to demonstrate how excessive gambling can lead to bankruptcy.

In 1851 the General Court of Virginia ruled that horse racing was defined in state law as more of a sport than a game, and bets for less than $20 were not prohibited by state anti-gaming laws at that time.

Two racetracks were built in Alexandria County (now named Arlington County) when it was still part of the District of Columbia. The Alexandria track operated approximately 1760-1810. The Mount Vernon track operated between 1841-1845, until it closed due to poor management.

In the 1800s, horse tracks did not make their profits simply by taking a small share of every wager. Instead, tracks and gamblers bet against each other. The tracks had a direct interest in which horses won. A dishonest track that “fixed” a race could generate a major profit. Corruption and Victorian standards of conduct led to a public reaction against gambling. The General Assembly banned gambling at horse tracks in early 1894 but included a major exemption for tracks on sites owned by agricultural associations or fairs, and driving clubs or parks. Those organizations were not expected to allow gambling dens for the lower classes. The gamblers who managed establishments at Jackson City in Alexandria County, on the southern end of Long Bridge, found a way to continue.

The Colonial Downs Group built a racetrack located in New Kent County, Virginia. The track conducted Thoroughbred flat racing and Standardbred harness racing between 1997 and 2014. September 1, 1997, they constructed one of the largest tracks in size in the country but built a relatively small clubhouse. They also built OTBs prior to the opening of the track. The tract of land on which the track is built was obtained through an eminent domain suit brought by the State of Virginia against an African American/Native American family (Tero Johnson) that had owned the majority of the land since 1863.

Until 2005, the track was managed by the Maryland Jockey Club under a complicated agreement with Virginia and Maryland regulators and the Maryland-Virginia Racing Circuit. The track ran two legs of the annual Jacobs Investments Grand Slam of Grass. This event consisted of the Colonial Turf Cup and the Virginia Derby from Colonial Downs, the Secretariat Stakes from Arlington Park, and the Breeders’ Cup Turf.

The schedule originally ran from June 12 to August 4, 2009, but was later moved up one week. This allowed the track to run live racing on Belmont Stakes day, June 6. The fall harness meet ran 36 dates, from September 8 through November 7. The harness meet was timed to end on Breeders’ Cup weekend. Colonial Downs has not offered thoroughbred racing since 2013, due to a dispute between track management and horsemen’s groups. Harness racing ended the following year, and all track-affiliated betting sites were closed in April 2015.

In April 2018, Virginia enacted a law to allow historical racing machines (similar to slot machines) at the track and at off-track betting parlors, in an effort to make it economically viable to reopen the track. Weeks later, the track was purchased by the Chicago-based group, Revolutionary Racing, who alongside other investors then formed the current Colonial Downs Group, who currently own the track. Colonial Downs will hold its first race since 2013 on August 8th, 2019.

The following graded stakes were formerly run at Colonial Downs:

• Grade 2 Colonial Turf Cup (since 2015, run at Laurel Park as the Commonwealth Turf Cup)
• Grade 3 All Along Stakes (since 2015, run at Laurel Park)
• Grade 3 Virginia Oaks (since 2015, run at Laurel Park as the Commonwealth Oaks)
• The Grade 2 Stake, Virginia Derby, which will return to Colonial Downs on August 31, 2019.