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.”
Hilly Chase Speaker Trevon Bryant Urges Students to Embrace Their Most Authentic Self
Mr. Bryant, a former NCAA Division I running back, delivered the first Hilly Chase of the 2024-2025 academic year on September 25
Trevon Bryant knew that his life had changed when his coach blew the whistle and shouted, “Move the ball up 10 yards.”
Trevon wanted to line up with his teammates for the next play. He wanted to stand next to the quarterback, ready to take the ball again.
But the game—and the dreams he had pursued since childhood—kept moving down the field without him.
The searing pain in his collapsed knee told him that his goal of becoming an NFL running back, his plan to earn enough money to take care of his mom and family back in St. Augustine, FL, and his intense desire to win the affection of his absent dad would all be sidelined.
Just seconds before, Trevon had put everything he had into securing a tough first down. Now he was realizing just how much that play had cost him.
In the days and weeks that followed, he sank into depression. He lost his sense of purpose. He lost his sense of identity, and with it, his sense of direction and his source of motivation. And for the first time since his father had walked out of his life, he felt that he didn’t matter.
But, as Mr. Bryant explained to the students and faculty assembled for the first Hilly Chase of the 2024-25 school year, that intense moment of personal loss is what led him to discover his authentic self.
Mr. Bryant, who is assistant dean of student life and a football coach at Deerfield Academy, noted that his sense of failure at that moment helped him recognize his true gifts: the power of his voice and his passion to help others discover who they are.
He emphasized that young people shouldn’t let the world define them. Today’s youth are surrounded by social definitions of success and failure—from body image, to friendships, to social media status, to family expectations—that often have little to do with what makes a person feel truly seen and valued.
He emphasized above all the importance of understanding “what makes you unique” because a person’s uniqueness is, ultimately, the most distinct and valuable thing that humans share with each other.