The Rye City School District website states (with justifiable pride) that its three elementary schools and Rye Middle School are all “National Blue Ribbon Schools of Excellence.” It also notes that Rye High School is ranked among the top high schools in the country by U.S. News and World Report and Newsweek magazine.
In addition to its successful public schools, the City of Rye is also home to three private schools: Rye Country Day School (K-12), Resurrection School (K-8), and School of the Holy Child (grades 5-12). To appreciate the importance of all these public and private academic resources for the community, it is useful to consider how far Rye’s primary and secondary education programs have progressed in the last 100 years.
The early village of Milton had a wooden school building (with a bell tower), which was built in the 1830s. That structure was moved to its current site at 630 Milton Road and is now a private residence. In the 1890s, Milton school students moved into a brick building, which has been expanded and updated several times.
Beginning in the early 1900s, Rye’s small high school shared space with Rye Grammar elementary school on land between School Street, Purdy Avenue, and Boston Post Road. A 1915 Rye Chronicle article stated that “Rye now has a school where manual training in many branches may be obtained.”
By the late 1920s, both elementary schools (Milton and Rye Grammar) were overcrowded, and the small high school did not have a gymnasium or an athletic field.
Finally, in 1929 (just two months before the stock market crashed) Rye taxpayers approved construction of a new high school for grades 7-12. By the time it opened in 1931, the cost was nearly $1.5 million, which is well over $20 million in today’s dollars.
As the population of Rye grew, the need for more elementary schools was met first by the addition of Midland, which opened in 1953, followed by Osborn School in 1957. Total enrollment in Rye public schools more than doubled from 1,475 in the 1951-52 school year to 3,171 some 20 years later.
In 1985, a plan for annexation of the Rye Neck schools into the Rye city school district was endorsed by both school boards, but busing and other concerns caused the proposal to be defeated. During the past 40 years, numerous improvements have been made to Rye’s public-school facilities at all levels along with a wide range of curriculum changes and extracurricular activities.
Rye has also benefited from the excellence of Rye Country Day School, which was formed in 1920 by the merger of Rye Seminary, a local girls’ school, with Rye Country School, a boys’ school in Harrison. In the 2025 ranking by Niche of “Best Private Schools in Westchester,” RCDS is ranked No. 1.
In 1958, the size of the RCDS campus was substantially reduced by construction of the I-95 corridor. However, the current 35-acre campus includes academic buildings, libraries, performing arts and creative arts centers, as well as an athletic center and sports fields.
Recently, RCDS announced plans for a major campus development, three years after the school acquired a nine-acre property across Boston Post Road from the New York State Thruway for $5.16 million. The purchase was made possible by legislation, sponsored by Rye Assemblyman Steve Otis, which stipulates that the proposed field, track, and ice rink on that property will be made available for public use 29 percent of the available hours.
Another private school alternative in Rye has long been provided by the Church of the Resurrection parish, which was established in 1880. Its first church was erected on Purchase Street in 1889, followed by completion of a parochial school building in 1908 on Boston Post Road, adjacent to the church. An all-girls school, the Academy of the Resurrection, was established in 1950, but closed in the early 1990s. However, Resurrection School continues, with coeducational classes from Pre-K through grade 8.
A more recent addition to school choices for Rye families is the School of the Holy Child. According to Wikipedia, it is “an all-girls, Catholic independent, college-preparatory school for grades 5 through 12, located in Harrison, New York (with a Rye postal address).” Originally located in Manhattan, the school moved to its current 20-acre campus on Westchester Avenue in 1957.
