The Winchendon School (TWS) is a coeducational, boarding and day school for grades 9-12 & PG. A day and boarding campus is located outside of Boston on over 300 acres in central Massachusetts, The Winchendon School is nestled between Mount Monadnock and Mount Wachusetts. A city day campus is located in New York City in Herald Square.
Our 285 students work collaboratively in small group settings.
Our program is designed to allow every student and their learning style to be known and celebrated.
Quick Stats (2025)
- Grades: 9-12, PG
- Enrollment: 285 students
- Yearly Tuition (Boarding Students): $70,900
- Yearly Tuition (Day Students): $35,500
- Acceptance rate: 40%
- Average class size: 8 students
- Application Deadline: Jan. 15 / rolling
- Source: Verified school update
Top Rankings
The Winchendon School ranks among the top 20 boarding schools (out of 281 schools) for:
School Overview
School Focus
College Preparatory
College Preparatory
School Type
Co-ed
Co-ed
Year Founded
1926
1907
Campus Size
326 acres
125 acres
Colors
White, Dark green, Kelly green
Student Body
Enrollment
285 students
315 students
% Students of Color
14%
26%
% International Students
25%
21%
% Students Boarding
75%
70%
Offers Post-Grad Year
Yes
No
Academics and Faculty
Saturday Classes
No
No
Student : Teacher Ratio
5:1
7:1
# of AP / Advanced Courses Offered
19
18
% Faculty with Advanced Degree
50%
72%
Summer Program Offered
No
Yes
Tuition Cost
Endowment Size
$30 million
$30 million
Yearly Tuition
(Boarding Students)
(Boarding Students)
$70,900
(7 and 5 day boarding available: 5-day $59750)
(7 and 5 day boarding available: 5-day $59750)
$67,000
Yearly Tuition
(Day Students)
(Day Students)
$35,500
$36,000
Yearly Tuition
(5 Day Boarding)
(5 Day Boarding)
$59,750
$49,400
% Students on Financial Aid
40%
40%
Avg. Financial Aid Grant
$20,000
$25,000
Admissions
Application Deadline
Jan. 15 / rolling
Jan. 15
SSAT Required
Yes
Yes
Acceptance Rate
40%
64%
Director of Admissions
John Toffey
Associate Director of Admissions
Erika Rothkegel
Application URL
AP / Advanced Courses
# of AP / Advanced Courses Offered
19
18
Courses
Biology, Calculus AB, Chemistry, Chinese Language and Culture, Comparative Government and Politics, Computer Science A, English Language and Composition, English Literature and Composition, Environmental Science, European History, French Language and Culture, Latin, Macroeconomics, Microeconomics, Physics, Psychology, Spanish Language and Culture, Statistics, US Government and Politics, US History
Sports
# Interscholastic Sports Offered
16
16
Extracurriculars
Total Extracurricular Organizations
17
23
Extracurriculars
Club or Organization:
Arts and Music Programs:
Recreational Athletic Programs:
Affinity Group, Community Service Club, Current Events & Debate, Green Key Student Ambassadors, Math Team, Model United Nations, National Honor Society, Newspaper, Robotics, Service Learning Groups, Student Government
Arts and Music Programs:
Recreational Athletic Programs:
College Matriculation
10 Most Popular College Choices (# Enrolled)
Northeastern University
6
Boston College
5
Boston University
4
Colby College
3
Cornell University
3
Hamilton College
2
Bowdoin College
1
Dartmouth College
1
Stanford University
1
United States Naval Academy
1
School Notes
- At The Winchendon School, we are guided by real-world learning. Classes are exciting and energetic; teachers reject lecturing and instead design active learning environments where students lead discussions, debate questions, and draw their own conclusions.
- We encourage academic risks, self-reflection, and practical learning. Whether studying street art in New York City, working on an internship studying gravitational waves at LIGO (Laser Interferometer Gravitational-Wave Observatory), or designing web animation, students are actively engaged in learning.
- Students connect studying to life beyond school, preparing them to be leaders and innovators. Backed by recent research, we know students learn better when they have strong connections with the people around them. The leaders of tomorrow must learn to connect with their communities locally and globally.
- Engaged learning begins with asking "Why?" The day is designed around the discovery of information and connecting to real-world issues. Students go beyond rote memorization of facts. Could you live on two dollars a day in Honduras? Why isn`t there enough food in the world, or is there? Learning to think big, take action, and have impact gives students a platform to tell a richer story about who they want to be and how they will impact the world.
- The Winchendon School accreditations: NEASC, NAIS
- Sample of notable school alumni/alumnae:
- Perry Dye ‘71 - Founder and president of Dye Designs. He is a world renowned golf course designer and has contributed to the design of hundreds of courses world wide. Golf Digest has ranked many of Perry’s courses at the top of their lists.
- Greg Selkoe ‘92 - Founder and CEO of XSET Former CEO/Founder of Karmaloop, Previously led Curateurs.com and former President of FaZe.
- Bruno Sundov ‘99 - The 7’3 inch student athlete from Split, Croatia had already been drafted in the NBA’s by the Dallas Mavericks in 1998, the year of the NBA Lockout. Because of the work stoppage, Bruno decided to attend The Winchendon School to learn English.
- Francisco Garcia ‘02 - Started at Winchendon, then moved on to play for Legendary Coach Rick Pitino at the University of Louisville. He was drafted in the first round of the 2005 NBA Draft by the Sacramento Kings and played for ten seasons in Sacramento, CA and Houston, TX.
- Lauren Kelly ‘14 - Was an outstanding student athlete starring in multiple sports signed a scholarship to attend Northeastern University to play for the Women’s Hockey Team. She is a former recipient of the Jason Ritchie Scholarship while at Winchendon and captain of the te
- Max MacKenzie ‘16 - Is an American actor, voice over artist, producer, and activist. After taking up acting at The Winchendon School, he debuted in his first film at the age of 18, in ‘Just Say Goodbye’ and also starred in an episode of Investigation Discovery’s highest rate
- Bryan Perla '17 - Caused a bidding war on Shark Tank for the product he developed while a student at The Winchendon School during ColLAB program.
- Sophie Jamison '18 - Known to millions of followers on social media as Sophie Lightning.
Source: Verified school update
Frequently Asked Questions
How much does The Winchendon School cost?
The Winchendon School's tuition is approximately $70,900 for boarding students and $35,500 for day students.
What schools are The Winchendon School often compared to?
The Winchendon Schoolis often viewed alongside schools like Cushing Academy by visitors of our site.
What is the acceptance rate of The Winchendon School?
The acceptance rate of The Winchendon School is 40%, which is lower than the boarding school average of 64%.
Who are famous alumni from The Winchendon School?
The Winchendon School famous alumni include: Perry Dye ‘71, Greg Selkoe ‘92, Bruno Sundov ‘99, Francisco Garcia ‘02, Lauren Kelly ‘14, Max MacKenzie ‘16, Bryan Perla '17 and Sophie Jamison '18.
What sports does The Winchendon School offer?
The Winchendon School offers 16 interscholastic sports: Alpine Skiing, Badminton, Baseball, Basketball, Cross Country, Cross Country Running, Dance, Golf, Ice Hockey, Lacrosse, Snowboarding, Soccer, Softball, Tennis, Ultimate Frisbee and Volleyball.
What is The Winchendon School's ranking?
The Winchendon School ranks among the top 20 boarding schools for Small average class sizes and High ACT scores.
When is the application deadline for The Winchendon School?
The application deadline for The Winchendon School is Jan. 15 / rolling (applications are due on Jan. 15 but additional applications are reviewed year-round as space permits ).
Alumni Reviews Review School
Review
Description
At the Winchendon School, small class sizes with no more than 8 or so students per class allow students valuable one on one time with teachers and more opportunities for participation during class. No students. . .
Small class size with support services and the golf course. . .
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Popular comparisons: The Winchendon School vs. Cushing Academy
People that viewed The Winchendon School also viewed these schools: Cushing Academy, Berkshire School, Northfield Mount Hermon, Deerfield Academy and The Williston Northampton School.
The nearest boarding school to The Winchendon School is Cushing Academy (6.9 miles away)
School
Location
Miles
Grades
Students
385 students 6.9 miles 39 School Street
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(978) 827-7300
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6.9
9-12, PG
385
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(413) 229-1003
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(413) 229-1003
80.2
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430
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(413) 498-3227
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(413) 774-1400
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(413) 774-1400
30.3
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653
400 students 42.9 miles 19 Payson Avenue
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(413) 529-3241
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(413) 529-3241
42.9
9-12, PG
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7-12, PG
400
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