It's always bittersweet, seeing the school supplies section coming back up in the stores and knowing that soon kids will no longer be everywhere. The oldest school in New York City was founded in 1628. The Collegiate School of New York City is an independent school for boys and is actually the oldest school in the United States. It is located on the upper west side of Manhattan and is a member of both the New York Interschool and the Ivy Prepatory school league. It hosts all grades k-12. and is ranked one of the best prep school for boys in the United States.