2. Trinity School, 1709

The Trinity School, which is also a private K-12 institution on the Upper West Side, is the fifth oldest school in the United States and welcomes both genders. Founded in 1709 as a school for charity supported by Anglican missionaries in 1709, classes initially took place at Trinity Church. In 1749, it had its first schoolhouse on the church grounds, making it the oldest “continuously operating educational institution in the city of New York.”

Founded by William Huddleston and available to both girls and boys at its founding, the school developed close ties to Columbia University (up next on this list) during its early years. By 1789, the school had 30 girls and 56 boys and no longer ran as a charity school. But in 1838, girls were prohibited and could no longer attend Trinity until 1971. In addition, it no longer receives endowments from Trinity Church, since it cut ties with the church in 1968.

While the school has continuously operated, it has changed locations quite a few times; in 1889 it moved to Madison Avenue and the next year moved to West 45th street.