Hillside School

About Us

Hillside School, in Marlborough, Massachusetts, provides a traditional, structured, and challenging academic environment for boys in grades 5-9. Our community is culturally diverse, with 145 students from 11 countries and all over the country. Hillside’s 150-acre campus, 35 miles west of Boston, provides an ideal setting for boys to excel academically, athletically, creatively and socially.  While we have excellent access to all the city has to offer, most learning takes place in classrooms with a 7:1 student to teacher ratio.

Standards and expectations are the guideposts for success at Hillside School. Our boys learn to embrace the School’s core values of compassion, determination, honesty, respect and fun at Hillside and beyond. These values prepare them for lives of meaning and purpose. Our boys’ efforts in achieving the Hillside core values are measured using our Shades of Blue system. This communication system monitors student progress and behavior, brings attention to areas of concern, and often prevents small issues from escalating. Shades of Blue is essential to Hillside’s effort to keep parents informed of their son’s academic and behavioral success and areas of challenge.

Hillside faculty draw upon their deep experience of knowing how boys learn, to meet every student at his individual learning threshold. Academics are thoughtfully designed to accommodate a spectrum of learning styles, from complex and accelerated courses, to programs designed for English as a Second Language students, to coursework that supports bright boys with particular areas of learning difficulty. One key characteristic of Hillside academic life is our shared commitment to teaching boys lifelong learning skills. They master how to take notes, read a text, study, and conduct research — so that when they graduate, they are genuinely and deeply prepared to tackle the challenges of their future learning.

Athletics promote group cooperation, socialization, self-confidence, school spirit, and play, as well as good physical, mental, and emotional health, all of which are essential to a child’s development.  The Hillside Athletic Program strives to instill sportsmanship, integrity, and effort through student participation. Coaches also emphasize value development.

Hillside’s nurturing environment provides the vital support every boy needs to learn and mature. Our community prides itself on knowing our students well, and we patiently guide our boys so they will develop a lasting foundation of compassion and self-esteem. Through our comprehensive yet flexible structure, as well as the professional experience that enables us to meet every boy at his own level of development, Hillside helps students navigate the uncertain world of early adolescence. Our graduates emerge as confident, independent learners and valued members of their communities.

Hillside School Fast Facts:

  • Founded: 1901
  • Enrollment: 145 Boys
  • Grades: 5-9
  • Class Size: 8-12 students
  • Day/Boarding Ratio: 35%/65%
  • Tutorial Support: Math, Language Arts, Organization, Social Skills
  • Tutorial Size: 2-4 students
  • Athletics: 22 competitive and non-competitive afternoon activities
  • Recent Secondary School Placement: St. Paul’s School, Phillips Exeter Academy, Williston Northampton School, Winchendon School, Choate Rosemary Hall, Dublin School, Lawrence Academy, New Hampton School, Kimball Union Academy, St. Mark’s School

3 Key Program Features:

  1. Hillside is on 150 acres in Marlborough, Massachusetts, located just 35 miles West of Boston, Massachusetts
  2. Our unique academic/leadership program, “Shades of Blue,” builds character, while holding students accountable to core values
  3. Academics are supplemented with small group tutorials in language arts, math, organization, and social skills for students needing support
  • Total Enrollment : 150
  • Type : All Boys
  • Boarding Grades : 5-9
  • Total Students : 150
  • Boarding Students : 105
  • Day Students : 45
  • ESL Offered : Yes
  • Summer Program : Yes
  • Avg. Class Size : 12
  • Standard Application : Yes
  • Academic URL : https://www.hillsideschool.net/
  • Sport URL :
Specialitiess
  • Entrepreneurship
  • Leadership