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For over 100 years, Hillside School has been teaching boys the core values of compassion, determination, honesty, respect, and brotherhood.

Founded in 1901 by sisters Charlotte and Mary Drinkwater, Hillside was originally located in Greenwich, MA. In 1927, the school was relocated to it's present-day location in Marlborough, MA. In October 2015, the school appointed its 10th headmaster, Ed Chase.

Since its founding, Hillside School has committed to offering an all-boys educational experience in a structured, inclusive, supportive environment. Our boarding and day program for boys in grades four through nine is unique in its ability to meet each student at his learning threshold and then truly maximize his potential, creating a transformative experience for our students.

Our Campus

Located on 150 acres, the Hillside campus is also home to an Innovation Lab, six dormitories, and housing for faculty and staff.

Our Students

Currently, 145 boys attend Hillside. 60% of our student population is made up of boarding students, hailing from 10 states and 10 foreign countries.

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Mission and Philosophy

Learn more about the mission and academic philosophy at Hillside.

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Start your experience by learning more about our Admissions process.

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Hillside's curriculum engages boys in the manner they learn best.

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Accreditations & Memberships

Hillside is proud to be a member of these leading independent school organizations: