Why would you send a sixth-grade boy to boarding school? Shouldn't a ninth-grade student start high school? What is a junior boarding school? Make an appointment to visit us today and learn why Eaglebrook, a boarding and day school for boys in middle school, might be the right place for your son.
Eaglebrook School was founded in 1922 by Howard Gibbs as a private boarding and day school for boys in middle school. Learn about our school in Deerfield, Massachusetts then and now, and read about the Core Skills we think every boy should know.
At Eaglebrook, we recognize that all students learn in different ways, vary in their innate abilities, and come from a variety of educational backgrounds. Classes at Eaglebrook are organized to meet the needs of each boy.
Eaglebrook is a close community of middle school students, teachers, and their families. Activities outside of the academic classroom are important to the intellectual, social, physical, and emotional development of boys in middle school. Learn about the programs we offer at Eaglebrook, from athletics to arts.
At Eaglebrook, boys learn more than they ever thought possible, discover inner resources, develop self-confidence, and have fun along the way. Delivering on our mission is only possible through the incredible generosity of alumni, parents, parents of alumni, and friends.”
Under blue skies and warm June sunshine, Eaglebrook welcomed alumni and their families back to the Hill for Reunion 2026.
This year's celebration honored classes ending in 1 and 6, bringing together generations of alumni to reconnect with classmates, revisit favorite campus landmarks, and reflect on the impact Eaglebrook continues to have on their lives.
Throughout the weekend, one message kept emerging from those who returned: “Come back”.
Whether attending a milestone reunion or simply making the trip to campus after years away, alumni spoke about the importance of returning to the place where lifelong friendships were formed and foundations were built. Conversations over meals, walks across campus, and time spent with former classmates served as reminders of the lasting connections that began during their years at Eaglebrook.
For many, Reunion is about more than revisiting memories. It is an opportunity to reconnect with the people who shared a formative chapter of life and to see how the values learned on the Hill continue to shape them decades later.
While the campus has evolved over the years, alumni noted that Eaglebrook's mission remains unchanged. The faces may be different, but the school's commitment to providing a supportive, challenging, and nurturing environment for boys continues to define the Eaglebrook experience.
During class gatherings and reunion remarks, alums reflected on the friendships, mentorship, and sense of belonging they found as students. Many shared how those experiences helped shape their confidence, character, and direction long after leaving Eaglebrook.
As the weekend ended, the sentiment was clear: Reunion is not just for milestone years. Alumni encouraged their classmates and fellow Eaglebrook graduates to return whenever they can—to walk the campus, reconnect with friends, and experience firsthand the enduring spirit of the Hill.
Thank you to all who joined us for Reunion 2026. We look forward to welcoming you back again soon.