Virginia Fall Races
Experience the horseracing traditions of Middleburg’s hunt country at the annual Virginia Fall Races, held the first Saturday and Sunday in October. Dating back to 1955, the steeplechase races take place at Glenwood Park, the oldest continually operated racecourse in the state. The event includes several regular races, as well as feature races like the Field Hunter Championship Finals, a mock fox hunt designed to showcase a variety of hunting skills. During the races, the park also hosts cocktail receptions and a family fun fair.