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Initially, Manhattan was settled by the Lenape Native Americans, who referred to the area nearby as “Muscota” or “Muscoota”, meaning “place of rushes”. The nearest Native American settlements were Rechewanis and Konaande Kongh in present-day Central Park, to the southeast of modern Morningside Heights. Additionally, a Native American path in the area was adapted into part of modern-day Riverside Drive. However, the region remained relatively hard to access because of the steep topography. Prior to the beginning of the 18th century, most travel within modern New York City was made via water, since there were few roads in the region.

Dutch settlers occupied Manhattan in the early 17th century and called the nearby area “Vredendal”, meaning “peaceful dale”. The western boundary of New Harlem was drawn through the present-day Morningside Park in 1666, running from 74th Street at the East River to 124th Street at the North River (now Hudson River) on the neighborhood’s western edge. The area to the west of the boundary, present-day Morningside Heights, was originally the common lands of British-occupied New York. In 1686, New York colonial governor Thomas Dongan granted the city of New York the patent to a triangular area between West 107th to 124th Streets, extending west to the Hudson River. The city sold the land to Jacob De Key in 1701. An easy connection to the rest of the modern-day city was made two years later, when Bloomingdale Road (modern-day Broadway) was extended north from Lower Manhattan to 117th Street. Harman Vandewater acquired part of the De Key farm by 1735, and it was called Vandewater Heights by 1738.

On September 16, 1776, the Battle of Harlem Heights was fought in the area, with the most intense fighting occurring in a sloping wheat field that is now the location of Barnard College. A plaque by the Columbia University gate on 117th Street and Broadway commemorates this battle. Vandewater Heights was sold by 1785 to James W. De Peyster. His brother, Nicholas De Peyster, bought the land directly to the west, along the shoreline.