Ossining Union Free School District is a school district headquartered in the Village of Ossining, Town of Ossining, New York. The district includes sections of the towns of Ossining and New Castle. Included within the portions of the school district in Ossining Town are Ossining Village and a section of Briarcliff Manor. About 28% of Briarcliff Manor is in the Ossining District, including Chilmark. As of 2017 Ray Sanchez is the superintendent: that year he won the "Superintendent to Watch" award.