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, community, and leadership help develop the soul and spirit of each student. Hillside School is committed to offering the educational experience in a structured, inclusive, supportive enviornment.
Lower School (K-3): Co-Ed Day Middle School (4-9): Boys, Boarding & Day
45 miles west of Boston 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.
Quick Facts (2026)
- Top-Ranked MA School
- Grades: Kindergarten-9
- Enrollment: 145 students
- 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:
Category
Attribute
School History
School Overview
Religious Affiliation
Grades Offered
Grades Kindergarten-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
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.: 31%
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
Tuition Notes
Day - $42,000
Day Intl - $46,620
5 Day - $59,900
5 Day Intl - $68,880
7 Day - $71,500
7 Day Intl - $83,000
% on Financial Aid
30%
Admissions Director
Sean Hayes
Application URL
Endowment Size
$5 million
Sports
Total Sports Offered
14 sports
Extracurriculars
Total ExtracurricularsTotal Extra-curric.
8 extracurriculars
ExtracurricularsExtra-curric.
Club or Organization:
Arts and Music Programs:
Recreational Athletic Programs:
Eco-TeamiLab
RocketryYearbook
Arts and Music Programs:
BandDrama
Recreational Athletic Programs:
AdventurePing-Pong
School Notes
- School Motto: To maximize the potential of every student in mind, body, and spirit.
- School Mascot: Bulldog
- Hillside seeks students who are looking for a structured, supportive, and challenging academic environment. Hillside also offers excellent support programs for students with mild learning disabilities or ADHD.
- Outstanding Secondary School placement at some of the nation's most selective schools, including Phillips Andover, Milton Academy, St. Marks, Groton, and Middlesex.
- Hillside is situated on 150 acres in Marlborough, Massachusetts. Marlborough is located just 45 miles West of Boston.The Farm at Hillside is utilized by students on a daily basis. Students participate in Farm Immersion twice a year and have the opportunity to work at the Farm every afternoon for their activity.Tutorials are available for students who need supplementation and a foundation of skills in Language Arts, Math, Executive Function, Social Skills and Foundations of Language.Hillside offers English as a Second Language for international students and Advanced Transition English for advanced English Language Learners.
- Sample of notable school alumni/alumnae:
- Terance Mann - NBA LA Clippers
Source: Verified school update
Frequently Asked Questions
Who are famous alumni from Hillside School?
Hillside School famous alumni include: Terance Mann.
What sports does Hillside School offer?
Hillside School offers 14 interscholastic sports: Alpine Skiing, Baseball, Basketball, Cross Country, Golf, Ice Hockey, Intramural Sports Only, Lacrosse, Rock Climbing, Snowboarding, Soccer, Tennis, Track and Field and Wrestling.
What is Hillside School's ranking?
Hillside School ranks among the top 20% of private schools in Massachusetts for: 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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