The first evidence of an organized school, in a building other than private homes is an old district school building, which ceased to be used in 1842 when the Chester Academy was built.

The Chester Academy was built in 1842 replacing the old district buildings and came under the jurisdiction of the Board of Regents in 1845, sharing in the distribution of the Literary Fund. It had a highly successful existence for many years and students from miles around came here to take Regents Examination.

Chester Union Free School District #1 was organized in the fall of 1869. The Academy, located on the corner of what is now Academy Avenue and 17M, served as the academic department.

The Chester Academy now houses grades 6-12 with the Middle School (6-8) separated from the High School (9-12). The Elementary School has undergone major renovations with an extended parking lot, new carpeting, and a wider lobby. It is now the home of grades K-5.

Students of Chester Schools have enjoyed the benefits of the small school atmosphere and have taken advantage of the opportunities to participate in a variety of activities including sports, drama, and student government. Countless students have gone from the Chester School experience to enjoy career and personal pursuits in a variety of places throughout the world.