Peekskill High School’s Class of 2024 has the distinction of being the school’s 100th graduating class.
Through the 1800s, two distinct school districts straddled MacGregory Brook. After 80 years of negotiation, the Oakside Union Free School District consolidated with the Drum Hill UFSD in April 1923. This year marks a century of classes graduating at Peekskill High School under one umbrella.
Officially, Peekskill’s two school systems operated under the oversight of Cortlandt as District 7 (Drum Hill) and District 8 (Oakside).
Peekskill’s dueling school systems date to at least 1820 and engaged in fierce rivalries over the years.
In February 1840, the districts officially merged, but the agreement fell apart five months later. “Pride, petty jealousies and school politics prevented” any cooperation, according to the city’s first historian, William T. Horton.
In 1848, voters in Drum Hill again proposed consolidation, but District 8, apparently, “was not receptive to the ideas and nothing happened,” according to an unpublished 1996 manuscript by Colin Naylor. Ten years later, déjà vu all over again.
By the 1920s, redundancies in salaries, operations and infrastructure became too impractical to justify as civic officials began the slow grind of divorcing Cortlandt and becoming a city.
The difference in wealth between the two areas – Drum Hill being more working class – stoked animosity and impeded any merger. In 1859, an anonymous letter in the Highland Democrat put it bluntly: “Their district is poor compared to ours… [and] the law of selfishness teaches us to keep what we have and get what we can.”
But in 1923, when voters weighed in 857 to 101 in favor of consolidation, 21 negative votes came from Oakside and 80 came from Drum Hill.
The new entity operated as a Union Free School District, which is unrelated to labor unions. The UFSD designation dates to a 1853 state law that encouraged smaller school districts to unite and create high schools.
After Peekskill achieved city status in 1940, officials switched to the City School District model in 1951 to gain more financial independence.
The two resilient but defunct educational entities established in the 1800s built several schools that are gone or closed, including Franklin Elementary (1902) and Park Street Elementary (1925).
The original Oakside School, completed in 1884, made way for the angular modern building that occupies the spot and now serves Second and Third Graders.
Uriah Hill, built in 1912, is filled with pre-Kindergarteners and Kindergarteners. Hillcrest and Woodside elementary schools date to 1954, three years after the city took over the school system, and share copycat architecture.
In 1859, the Drum Hill school district bought land and built a brick schoolhouse the following year. In 1911, after its demolition, the district completed construction on a new building, first used as a high school. It is now the Drum Hill Senior Living Center.
The structure became the Junior High School in 1931 after the consolidated district built a now-demolished high school where the middle school (completed in 2009) now stands.
Peekskill High School moved from Drum Hill to Oak Hill in 1972, replacing the razed remains of the Peekskill Military Academy, founded in 1833 and shuttered in 1968. The district’s administration building, Ford Hall (built in 1926), is the academy’s last vestige and contains a 500-seat auditorium.
Peekskill City School District Centennial Gala
A Centennial Gala at Factoria at Charles Point in April 2024 raised $25,000 for the Peekskill Education Foundation to fund five $5,000 Centennial Scholarships for graduating seniors.
