Hillside's mission to maximize each student's potential is achieved through our small class size, 7:1 student-teacher ratio, and our academic support programs tailored to meet each boy's needs.
Our extracurricular programs develop and challenge each student to perform at his highest level through practice, competition, and outstanding teacher support.
Spiritually, the school's focus on others, empathy, brotherhood, and leadership help develop the soul and spirit of each student.
Hillside is an all boys junior boarding and day school only 45 miles west of Boston serving 4th through 9th grade students.
We provide a structured, supportive, and challenging academic environment and our innovative teaching for the 21st-century skills prepares our boys for secondary school and beyond.
The academic program is supplemented with the renowned Wicks Tutorial Center with certified learning specialists providing small group tutorials offered in language arts, math, executive function, and social skills, for those students needing extra support.
Boarding and day students enjoy a rich curriculum that includes a broad after school program including competitive athletics, extracurricular activities, the Innovation Lab, and the Hillside Farm.
Our unique academic and leadership program, Shades of Blue, builds character while holding our students accountable to our core values.
Community inclusiveness is our hallmark; we welcome you to come to see for yourself.
Please visit us online for more information, and to schedule a visit today.
Quick Facts (2025-26)
- Top Ranked MA School
- Grades: 4-9
- Enrollment: 145 students
- Yearly Tuition: $69,500
- Average class size: 12 students
- Application Deadline: None / Rolling
- Source: Verified school update
Top Rankings
Hillside School ranks among the top 20% of private schools in Massachusetts for:
School Overview
Religious Affiliation
Grades Offered
Grades 4-9
ADD/ADHD Support
Yes
Learning Difference Programs
Yes
Learning Programs Supported
Language-based and Mild Learning Differences
Dual Language Immersion Program
Secondary Immersion Language
Other
Year Founded
1901
School Calendar
First Day of School
Tue. Sep 9, 2025
Last Day of School
Thu. May 28, 2026
Campus Size
150 acres
Student Body
Total Students
145 students
Student Body Type
% Students of Color
14%
State avg.: 30%
Students by Grade

Academics and Faculty
% Faculty w/Advanced Degree
32%
Average Class Size
12 students
List of Courses Offered
Matriculation DataMatric. Data
Classroom Dress Code
Formal
Dress shirt, tie or bow tie and dress pants with blazer.
Tuition and Acceptance Rate
Admission Deadline
None / Rolling
Yearly Tuition Cost
$69,500
Tuition Notes
Day - $40,400
5 Day - $59,900
7 Day - $68,500
7 Day International - $76,600
% on Financial Aid
32%
Admissions Director
Sean Hayes
Application URL
Endowment Size
$5 million
Sports
Total Sports Offered
15 sports
Extracurriculars
Total ExtracurricularsTotal Extra-curric.
9 extracurriculars
ExtracurricularsExtra-curric.
Club or Organization:
Arts and Music Programs:
Recreational Athletic Programs:
CookingEco-Team
iLabRocketry
Yearbook
Arts and Music Programs:
BandDrama
Recreational Athletic Programs:
AdventurePing-Pong
School Notes
- School Motto: Hillside’s mission is to maximize the potential of every student in mind, body, and spirit.
- School Mascot: Bulldog
- Hillside School provides a structured, supportive, and challenging academic environment for boys in grades 4-9. Boarding and day students enjoy a rich curriculum that includes a vibrant visual and performing arts program and competitive athletics. Our unique academic and leadership program, "Shades of Blue," builds character, while holding our students accountable to our core values. The Academic program is supplemented with small group tutorials offered in language arts, math, organization, and social skills for those students needing extra support. Our community is our hallmark; we welcome you to come see for yourself. Please visit www.hillsideschool.net for more, and to schedule a visit today.
- Sample of notable school alumni/alumnae:
- Terance Mann - NBA LA Clippers
Source: Verified school update
Frequently Asked Questions
How much does Hillside School cost?
Hillside School's tuition is approximately $69,500 for private students.
Who are famous alumni from Hillside School?
Hillside School famous alumni include: Terance Mann.
What sports does Hillside School offer?
Hillside School offers 15 interscholastic sports: Alpine Skiing, Baseball, Basketball, Cross Country, Golf, Ice Hockey, Intramural Sports Only, Lacrosse, Rock Climbing, Sailing, Snowboarding, Soccer, Tennis, Track and Field and Wrestling. Hillside School is ranked as one of the top 20% of private schools in Massachusetts for most sports offered.
What is Hillside School's ranking?
Hillside School ranks among the top 20% of private schools in Massachusetts for: Most sports offered and Oldest founding date.
When is the application deadline for Hillside School?
The application deadline for Hillside School is rolling (applications are reviewed as they are received year-round).
School Reviews
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