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.
51³Ô¹ÏÍø 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 Stats (2025)
- Grades: 4-9
- Enrollment: 145 students
- Yearly Tuition (51³Ô¹ÏÍø Students): $69,500
- Yearly Tuition (Day Students): $40,400
- Acceptance rate: 70%
- Average class size: 10 students
- Application Deadline: None / Rolling
- Source: Verified school update
Top Rankings
Hillside School ranks among the top 5 all-boys schools (out of 30 all-boys schools) for:
Category
Attribute
Community Size
School Overview
Definition of Terms | 2024 School Data
Hillside School
School Focus
Grades Offered
4-9
School Type
ADD/ADHD Support
Supports (LD)
Learning Difference Programs
in Reading, Writing, and Math
Religious Affiliation
Year Founded
1901
Campus Size
150 acres
Student Body
Enrollment
145 students
% Students of Color
14%
% International Students
38%
% Students 51³Ô¹ÏÍø
60%
Academics and Faculty
Saturday Classes
No
Classroom Dress Code
Formal
Button-down shirt, tie/bow tie and dress/khaki pants, dress shoes.
Button-down shirt, tie/bow tie and dress/khaki pants, dress shoes.
Average Class Size
10 students
Student : Teacher Ratio
7:1
ESL Courses Offered
% Faculty with Advanced Degree
50%
Summer Program Offered
No
Tuition Cost
Endowment Size
$5 million
Yearly Tuition
(51³Ô¹ÏÍø Students)
(51³Ô¹ÏÍø Students)
$69,500
(7-Day Domestic)
(7-Day Domestic)
Yearly Tuition
(Day Students)
(Day Students)
$40,400
(Domestic Day)
(Domestic Day)
Tuition international students
$79,100
Yearly Tuition
(5 Day 51³Ô¹ÏÍø)
(5 Day 51³Ô¹ÏÍø)
$59,900
% Students on Financial Aid
30%
Merit Scholarships Offered
Admissions
Application Deadline
None / Rolling
Accepts Standardized Application ( and/or )
Acceptance Rate
70%
Director of Admissions
Sean Hayes
Application URL
Sports
# Interscholastic Sports Offered
17
Extracurriculars
Total Extracurricular Organizations
18
Extracurriculars
Club or Organization:
Arts and Music Programs:
Recreational Athletic Programs:
3 v 3 Basketball, Band, Chess Club, Dart Club, Drawing Club, Kickball, Media Club, Ping-Pong, Prefect, Proctor, Yearbook
Arts and Music Programs:
Recreational Athletic Programs:
College Matriculation
10 Most Popular College Choices (# Enrolled)
School Notes
- 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.
- LD types supported: in Reading, Writing, and Math
- Hillside School accreditations: The Association of Independent Schools in New England (AISNE) and The Association of 51³Ô¹ÏÍø Schools (TABS)
- Sample of notable school alumni/alumnae:
- Terance Mann '12 - American Professional Basketball Player for the Los Angeles Clippers
- School Motto: To maximize the potential of every student in mind, body, and spirit.
- School Mascot: Bulldog
Source: Verified school update
Frequently Asked Questions
How much does Hillside School cost?
Hillside School's tuition is approximately $69,500 for boarding students and $40,400 for day students.
What is the acceptance rate of Hillside School?
The acceptance rate of Hillside School is 70%, which is higher than the boarding school average of 64%.
Who are famous alumni from Hillside School?
Hillside School famous alumni include: Terance Mann '12.
What sports does Hillside School offer?
Hillside School offers 17 interscholastic sports: Alpine Skiing, Baseball, Basketball, Cross Country, Cross Country Running, Golf, Ice Hockey, Lacrosse, Rock Climbing, Sailing, Skiing, Snowboarding, Soccer, Tennis, Track, Track and Field and Wrestling.
What is Hillside School's ranking?
Hillside School ranks among the top 20 boarding schools for Small student body (number of students).
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).
Related Schools
Show me:
People that viewed Hillside School also viewed these schools: The Bement School, Cardigan Mountain School, Fay School, Rectory School and North Country School.
The nearest boarding school to Hillside School is New England Innovation Academy (1.0 miles away)
School
Location
Miles
Grades
Students
226 students 52.7 miles 94 Old Main Street, PO Box 8
Deerfield, MA 01342
(413) 774-4209
Deerfield, MA 01342
(413) 774-4209
52.7
3-9
K-9
K-9
226
235 students 94 miles 62 Alumni Drive
Canaan, NH 03741
(603) 523-3548
Canaan, NH 03741
(603) 523-3548
94
6-9
235
250 students 36.7 miles P.O. Box 68 528 Pomfret Street
Pomfret, CT 06258
(860) 928-1328
Pomfret, CT 06258
(860) 928-1328
36.7
5-9
PK-9
PK-9
250
88 students 173.2 miles 4382 Cascade Road
Lake Placid, NY 12946
(518) 523-9329
Lake Placid, NY 12946
(518) 523-9329
173.2
4-9
88
Recent Articles
How to Choose the Right Performing Arts 51³Ô¹ÏÍø School: A Checklist for Parents and Students
Every year, thousands of gifted young artists apply to top performing arts boarding
schools, yet most families approach the selection process without a clear roadmap. Knowing what to look for—from teacher qualifications to alumni success rates—makes all the difference in finding a program where you can truly flourish.
The 51³Ô¹ÏÍø School Glossary
51³Ô¹ÏÍø schools have their own jargon just like any activity or affinity group has.
A Glimpse into 51³Ô¹ÏÍø School Life at Hawai‘i Preparatory Academy
One of the most common questions families ask when exploring boarding school options is: What does a typical day look like for a student? Beyond academics, they want to understand how students live, learn, and grow within the community—how daily routines shape not only their education but also their independence, friendships, and character.
