Hillside School
Marlborough, Massachusetts
404 Robin Hill Street Marlborough, MA 01752
Junior Boarding at Hillside School
Hillside School is an independent day and boarding school in Marlborough, Massachusetts, known for its structured, supportive, and nurturing educational environment. Founded in 1901 by sisters Charlotte and Mary Drinkwater, Hillside has more than a century of experience helping students grow into confident, capable learners and compassionate young people.
Hillside serves students in two thoughtfully designed divisions. The Lower School welcomes co-educational day students in grades K–3, where children build a strong academic foundation while developing curiosity, confidence, and positive social skills. Small class sizes and individualized attention ensure that each child is known, supported, and encouraged from the very start of their educational journey.
The Middle School serves boys in grades 4–9 as both day and boarding students. This program is intentionally designed to meet boys at a critical stage of development, combining rigorous academics with clear structure and meaningful support. Teachers tailor instruction to individual learning styles, helping students strengthen executive function skills, independence, and self-advocacy. Beyond the classroom, students engage in athletics, the arts, and experiential learning that promote teamwork, leadership, and personal growth.
Across both divisions, Hillside emphasizes character education, responsibility, and community. Faculty members build strong relationships with students, guiding them academically and personally while fostering resilience and confidence.
Enrollment
145 Enrolled
Grades Offered
Enrolling: Grades K-9
Boarding: Grades 4-9
School Mission
Hillside’s mission is to maximize the potential of every student in mind, body, and spirit, preparing graduates to excel both in secondary school and beyond.
“Hillside has been a wonderful experience for our son… Our son has learned independence, personal responsibility and leadership. He has made friends from around the country and around the world. The structured experience has helped him grow as a student academically as well. As he put it ‘I finally have learned how to learn’… Hillside had been a great next step for him as a student, an athlete and a man.”
Hillside School Parent
Junior Boarding at Hillside School
Hillside School is an independent day and boarding school in Marlborough, Massachusetts, known for its structured, supportive, and nurturing educational environment. Founded in 1901 by sisters Charlotte and Mary Drinkwater, Hillside has more than a century of experience helping students grow into confident, capable learners and compassionate young people.
Hillside serves students in two thoughtfully designed divisions. The Lower School welcomes co-educational day students in grades K–3, where children build a strong academic foundation while developing curiosity, confidence, and positive social skills. Small class sizes and individualized attention ensure that each child is known, supported, and encouraged from the very start of their educational journey.
The Middle School serves boys in grades 4–9 as both day and boarding students. This program is intentionally designed to meet boys at a critical stage of development, combining rigorous academics with clear structure and meaningful support. Teachers tailor instruction to individual learning styles, helping students strengthen executive function skills, independence, and self-advocacy. Beyond the classroom, students engage in athletics, the arts, and experiential learning that promote teamwork, leadership, and personal growth.
Across both divisions, Hillside emphasizes character education, responsibility, and community. Faculty members build strong relationships with students, guiding them academically and personally while fostering resilience and confidence.
School Facilities
Located on a scenic 150-acre campus in Marlborough, Massachusetts, Hillside School offers students a unique balance of space, nature, and accessibility. Just 45 minutes west of Boston, the school provides a peaceful, purpose-built academic environment while remaining close to the city for enriching day trips, cultural experiences, and experiential learning opportunities. Hillside’s expansive campus includes athletic fields, nature trails, a working farm, an Innovation Lab, and residential dormitories, giving students room to learn, explore, and grow in a safe and engaging setting.
Academics
Hillside School offers a rigorous, student-centered program focused on personalized learning, critical thinking, and global awareness. Small classes allow teachers to tailor instruction across core subjects. As an IB World School, Hillside delivers the IB Middle Years Programme, emphasizing inquiry, interdisciplinary learning, and real-world application. Academic support is enhanced through the Tutorial Center, and hands-on experiences in the Innovation Lab, preparing students for success in secondary school and beyond.
Athletics
Hillside’s athletics program promotes physical fitness, teamwork, and personal growth. Students participate in a wide range of interscholastic sports throughout the fall, winter, and spring seasons, including soccer, cross country, basketball, baseball, lacrosse, and more. Dedicated coaches emphasize skill development, sportsmanship, and healthy competition, encouraging students to challenge themselves, build confidence, and develop perseverance. Athletics play an important role in reinforcing Hillside’s core values of respect, resilience, and community engagement.
Arts
The arts program at Hillside nurtures creativity and self-expression across visual arts, music, and performing arts. Students explore drawing, painting, sculpture, and other media while developing technical skills and artistic confidence. In music and performance, students participate in ensembles, explore instruments, and take part in theatre productions that strengthen collaboration, expression, and stage presence. The arts complement academic and athletic pursuits by fostering imagination, cultural appreciation, and personal voice.
Signature Program(s)
Hillside’s signature programs blend innovation, strong academics, and personalized support. The Innovation Lab (iLab) fosters creativity and hands-on problem solving, while the Tutorial Program builds academic skills, organization, and self-advocacy. The IB Middle Years Programme is strengthened by individualized instruction that promotes confidence and independence. An international student community broadens cultural perspectives, and comprehensive secondary school guidance supports families in finding the right high school fit.
Summer Programs
