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By 1000 AD, Woodland Indians known as the Lenape began permanent settlements from lower New York State through Delaware. The Wiechquaskeck Lenapes occupied this site, settling into an agricultural lifestyle. They hunted in wooded uplands, fished in Tibbetts Brook, farmed on the Parade Ground and Indian Field and foraged through meadows and forests for nuts, fruits and other edible plants.

In 1639, the Dutch East India Company brought the first Europeans to settle in the Bronx, purchasing most of today’s Bronx County from the local Natives and, in 1646, sold it to Holland native Adriaen Van Der Donck, who became the first single owner of what is now Van Cortlandt Park. His vast estate “de Jonkeerslandt“ gave Yonkers its name. The land passed through several families, each gradually developing it into viable farmland and a working plantation.

The Van Cortlandt name was first associated with the tract of land bounded by modern Yonkers City Line between Broadway, Jerome Avenue, and Van Cortlandt Park East in 1694, when Jacobus Van Cortlandt bought the property. During the 1690s the enslaved Africans he owned dammed Tibbetts Brook to create a 16–acre lake to power the gristmill. The Van Cortlandt Mansion was built in 1748, also by enslaved Africans, for his son, Frederick Van Cortlandt. Frederick’s family occupied the land until the 1880s. Frederick also established the family burial plot on Vault Hill where, at the onset of the American Revolution, City Clerk Augustus Van Cortlandt hid the city records from the British Army. Slaves, both African and Native Peoples, would have been laid to rest at a lower level closer to the lake.

The 19th century brought projects to the future parkland that reflected the city’s growth. The 41–mile–long Croton Aqueduct was the first public work built through the site in 1837, bringing water from Westchester County to the site currently occupied by the main branch of the New York Public Library at 42nd Street in Manhattan. The Old Croton Aqueduct Trail stretches for 1.1 miles atop the portion of the aqueduct in Van Cortlandt Park.

In the 1880s, two railroad lines were laid across the parkland. The Putnam Railroad Line established service to Brewster and points north. A spur of this line provided a quick trip northwest through the park to Yonkers’ Getty Square. The Park’s 1.5–mile section of the Putnam Greenwayl enables hikers to experience sturdy bridges traveled by trains when the rail lines were active.

During the 1940s and 50s, highway construction—another by–product of the region’s growth—cut through the park and resulted in loss of precious wetlands and increased difficulty in traversing the park.

In September 2004, following years of research, discussion and debate, the New York City Council allowed the City to construct a water filtration plant for the Croton Water Supply under the Mosholu Golf Course in Van Cortlandt Park. As part of the agreement, the Parks Department received more than $200 million from the Department of Environmental Protection for improvements to over 70 Bronx parks. Creation of Sachkerah Woods Playground was one of the first Croton mitigation projects completed in the borough, and the first in Van Cortlandt Park.

Well after the Civil War, the Van Cortlandt property and plantations in the area fell into disrepair and became overgrown. The City of New York acquired this parkland in 1888 but did not name it in honor of the Van Cortlandt family until 1913. Over time, it developed some sections, added play areas, made wild areas passable and upgraded existing features. The first municipal golf course in the country opened in Van Cortlandt Park in 1895; a second, the Mosholu Golf Course, opened in 1914. As municipal golf courses, Jewish and African Americans were allowed to play for the first time. By a special act of the New York State Legislature, the Van Cortlandt Mansion was leased by the City to The National Society of Colonial Dames in the State of New York and the historic house opened as a museum in 1897 under the stewardship of ‘The Dames.’ The plantation’s wheat fields became, the Parade Ground in 1901, and National Guard used it for training exercises until the end of World War I. In 1906, on the east side of the park, The Bronx Chapter of the Daughters of the American Revolution dedicated a cairn of stones as a memorial to Chief Daniel Nimham, his son Captain Abraham Nimham, and 17 other Stockbridge Indians who were slain there during the Revolutionary War.

In 1913, the Cross Country Running Course opened, featuring both 5–mile and 3–mile loops. Van Cortlandt Stadium opened in 1939, and three years later the Getty Square spur of the New York Central Railroad was removed and the property given back as parkland. The current horse stables and adjoining bridle path opened in 1955. Three named nature trails added in the 1980s and 90s offer hikers the opportunity to explore the wetlands and forests of the park. The Cass Gallagher Nature Trail is dedicated to a longtime Bronx resident and environmental activist, and the John Kieran Nature Trail commemorates a famed naturalist and newspaperman. In 1997, the first east–west connector trail was established and named for renowned naturalist John Muir who founded the Sierra Club.

The NYC Parks’ Administrator’s Office was established in 1983 to oversee all operations, maintenance and management. In 1992, a group of Bronx residents formed the Friends of Van Cortlandt Park. In 2009, the Van Cortlandt Park Conservancy was formed as a public/private partnership with NYC Parks. In 2019, the Friends of Van Cortlandt Park and the Van Cortlandt Park Conservancy joined together to create the Van Cortlandt Park Alliance, a superior stewardship organization to guide the future of Van Cortlandt Park and the implementation of the 2034 Master Plan.