Hillside seeks students who are looking for a structured, supportive, and challenging academic environment.
Excellent programs for students with minor learning disabilities or ADD/ADHD. Hillside is situated on 150 acres in Marlborough, Massachusetts. Marlborough is located just 35 miles West of Boston.
The Farm at Hillside is utilized by students on a daily basis. Students also 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 remediation and a foundation of skills in Language Arts, Math, Organization, Social Skills and Foundations of Language.
Hillside offers English as a Second Language for international students and Business English for advanced English Language Learners.
Quick Stats (2025)
- Top Ranked MA School
- Grades: 4-9
- Enrollment: 142 students
- Yearly Tuition: $65,800
- Average class size: 10 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
Year Founded
1901
Summer School Offered
Yes
School Calendar
Student Body
Total Students
142 students
Student Body Type
% Students of Color
24%
State avg.: 29%
Students by Grade

Academics and Faculty
Total Classroom Teachers
30 teachers
Student : Teacher Ratio
5:1
National avg.: 13:1
% Faculty w/Advanced Degree
50%
Average Class Size
10 students
List of Courses Offered
Matriculation DataMatric. Data
Classroom Dress Code
Formal
Dress shirt and tie, Khaki pants
Tuition and Acceptance Rate
Admission Deadline
None / Rolling
Yearly Tuition Cost
$65,800
Tuition Notes
Day - $39,900
5 Day - $58,900
7 Day - $68,500
7 Day International - $76,600
% on Financial Aid
32%
Admissions Director
Sean Hayes
Endowment Size
$5 million
Sports
Total Sports Offered
15 sports
Extracurriculars
Total ExtracurricularsTotal Extra-curric.
9 extracurriculars
ExtracurricularsExtra-curric.
Club or Organization:
Cooking, Eco-Team, iLab, Rocketry, Yearbook
Arts and Music Programs:
Band, Drama
Recreational Athletic Programs:
Adventure, Ping-Pong
Cooking, Eco-Team, iLab, Rocketry, Yearbook
Arts and Music Programs:
Band, Drama
Recreational Athletic Programs:
Adventure, Ping-Pong
School Notes
- Hillside School provides a structured, supportive, and challenging academic environment for boys in grades 5-9. 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 $65,800 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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