The land that Van Cortlandt Park now occupies was once a vast grain plantation, owned by Frederick Van Cortlandt (1699–1749) and family. In 1748, he built what is now known as the Van Cortlandt House on the property, but died before its completion. Frederick willed the massive home and surrounding lands to his son, James Van Cortlandt (1727–1787).
The Van Cortlandt family land was used during the Revolutionary War by Rochambeau, Lafayette, and Washington. It was in this area that the Stockbridge militia was destroyed by the Queen’s Rangers; a stone memorial was placed at “Indian Field” in 1906.
In 1888, the family property was sold to the City of New York and made into a public parkland, with the majority of the grain fields converted into a sprawling lawn dubbed “The Parade Ground”. The Van Cortlandt House was converted into a public museum and, with the city’s approval, particularly overgrown areas of the property were made passable. Wide walking paths were built over original walkways, including the thin paths that led to the Van Cortlandt family cemetery, high on the nearby bluffs.
The Van Cortlandt Golf Course, the nation’s first public golf course, opened in 1895 and is located on the park grounds. The “Parade Ground” north of the museum is one of New York’s principal cricket fields. A bicycling path runs through the woods between this lawn and the golf course, northward along Tibbets Brook and the former New York and Putnam Railroad line into Yonkers. Another runs east from the golf course’s clubhouse to connect to the Mosholu Parkway bike path. The Old Croton Aqueduct Trailway begins in Van Cortlandt Park.
Van Cortlandt Park is a popular site for cross country running owing to its miles of cinder trails, race courses, and hills. The path surrounding the Parade Grounds known to runners as the “flats,” is 1.37 miles (2.2 km) around. The infamous “back hills” provide a 1.3-mile (2.1 km) loop in the northwestern section of the park.
The park is used for the Northeast regional championships of the Foot Locker Cross Country Championships as well as numerous college championships each fall. The famed 2.5-mile (4 km) course is used for most high school races, including the Manhattan Invitational, one of the largest high school cross country meets in the nation. In 2006, the USA Cross Country Championship was held at Van Cortlandt.