Founded in 1794, Cheshire Academy is a coed boarding and day school for students in grades 9-12 plus Postgraduate (PG).
At Cheshire Academy, starting with the 2022-2023 academic year, day tuition is reduced by nearly a third to be better aligned with the income levels of more families within the region. Boarding tuition is reduced by 10%
In addition to traditional 7-day boarding, Cheshire Academy offers students a 5-day boarding option, allowing them to be at home for weekend commitments such as athletics, arts, family, and community onbligations.
Ranked in the Top 10% "Best College Prep Private Schools in America" and Top Third "Best Boarding Schools in America" (Niche 2023)
The historic 104-acre campus is nestled in the bucolic but central town of Cheshire, Conn., just two hours drive from both Boston and New York City.
With 343 students from 14 states and 27 countries, CA takes a flexible and tailored approach, allowing students to combine a variety of academic and extracurricular offerings optimal to their individual needs, strengths, and interests.
CA offers personalized learning opportunities like the Roxbury Academic Support Program, the International Baccalaureate (IB) Program and Art Major Program.
Cheshire Academy has 17 sports and 27 teams for boys and girls. There are also non-competitive athletic activities to ensure all students have an enjoyable and physically active experience. Cheshire Academy has produced professional athletes as well as countless collegiate athletes.
Students become culturally-sensitive and internationally-minded, and develop the critical thinking skills, confidence, and character that enable them to succeed in college and as citizens of a global society.
Quick Stats (2025)
- Grades: 9-12, PG
- Enrollment: 343 students
- Yearly Tuition (Boarding Students): $57,250
- Yearly Tuition (Day Students): $29,850
- Acceptance rate: 45%
- Average class size: 10 students
- Application Deadline: Feb. 1 / rolling
- Source: Verified school update
Top Rankings
Cheshire Academy ranks among the top 20 boarding schools (out of 277 schools) for:
Category
Attribute
Offering Breadth
School History
School Overview
School Focus
College Preparatory
College Preparatory
School Type
Co-ed
Co-ed
Year Founded
1794
1907
Campus Size
104 acres
125 acres
School Motto
From Here to Anywhere
School Calendar
Last Day of School
Sun. Jun 1, 2025
Student Body
Enrollment
343 students
319 students
% Students of Color
34%
27%
% International Students
27%
20%
% Students Boarding
52%
70%
SAT range (25th-75th percentile)
1070 - 1390
-
Offers Post-Grad Year
Yes
No
Academics and Faculty
Saturday Classes
No
No
Classroom Dress Code
Casual
Dress is "academic dress" (one step above casual) Monday, Tuesday, and Thursday, with casual Wednesdays (CA spirit wear) and formal Fridays (a historic tradition).
Dress is "academic dress" (one step above casual) Monday, Tuesday, and Thursday, with casual Wednesdays (CA spirit wear) and formal Fridays (a historic tradition).
Casual
Student : Teacher Ratio
6:1
7:1
# of AP / Advanced Courses Offered
45
18
Number of IB Courses Offered
36
-
ESL Courses Offered
No
Yes
% Faculty with Advanced Degree
73%
72%
Summer Program Offered
No
Yes
Tuition Cost
Endowment Size
$16.3 million
$30 million
Yearly Tuition
(Boarding Students)
(Boarding Students)
$57,250
(Reduced by 10% for 2022-23.)
(Reduced by 10% for 2022-23.)
$66,900
Yearly Tuition
(Day Students)
(Day Students)
$29,850
(Reduced by nearly one third for 2022-23.)
(Reduced by nearly one third for 2022-23.)
$36,000
Tuition international students
$67,250
$57,650
Yearly Tuition
(5 Day Boarding)
(5 Day Boarding)
$55,250
$49,300
% Students on Financial Aid
43%
40%
Avg. Financial Aid Grant
$23,971
$25,000
Admissions
Application Deadline
Feb. 1 / rolling
Jan. 15
Acceptance Rate
45%
64%
Director of Admissions
Rebecca Brooks
Application URL
AP / Advanced Courses
# of AP / Advanced Courses Offered
45
18
Courses
AP Calculus I-AB, AP Music Theory, AP Psychology, AP Statistics, Arts Major Program, IB Biology SL & HL1/HL2, IB Chemistry SL1/SL2 & HL1/HL2, IB Computer Science SL1/SL2, IB Economics SL1/SL2, IB English Language & Literature HL1/2 & SL1/2, IB English Literature HL1/2 & SL1/2, IB Environmental Systems and Society SL, IB French ab Initio 1/ab Initio 2, IB French SL1/SL2 & HL1/HL2, IB History of the Americas SL1/SL2 & HL1/HL2, IB Lit & Performance SL1/SL2, IB Mandarin ab Initio 1/ab Initio 2, IB Mandarin SL1/SL2, IB Math SL2/HL2, IB Math Studies SL2, IB Mathematics: Analysis and Approach SL1, IB Mathematics: Applications and Interpretation SL1, IB Music SL1/SL2 & HL1/HL2, IB Physics SL1/SL2 & HL1/HL2, IB Spanish SL1/SL2 & HL1/HL2, IB Sports/Exercise/Health Science SL, IB Theater SL1/SL2, HL1/HL2, IB Theory of Knowledge Y1/Y2, IB Visual Arts SL1/SL2 & HL1/HL2
Sports
# Interscholastic Sports Offered
15
16
Extracurriculars
Total Extracurricular Organizations
39
23
Extracurriculars
Club or Organization:
Admission Ambassadors, Astronomy Club, Black Girl Coalition, Black Student Union, Candy Club, Ceramics Club, Chess Club, Community Service Club, Debate Club, Eco-Leaders, Future Business Leaders of America, Garden Club, Gender Sexuality Alliance, Ich Dien Society, Kindness Club, Magic: The Gathering Club, Manga/Anime, Math Club, Model United Nations, National Honor Society, New England Math League, Peer Counselors, Photography Club, Prefects, Robotics Club, Science Olympiad, Spirit Squad, Student Activities Committee (SAC), Student Equity Team, The Coleman Group, The Transformers, Yearbook
Arts and Music Programs:
Jazz Ensemble, Rock Band, String Ensemble
Recreational Athletic Programs:
Fencing - recreational, Golf - recreational, Strength and Conditioning, Tennis - recreational
Admission Ambassadors, Astronomy Club, Black Girl Coalition, Black Student Union, Candy Club, Ceramics Club, Chess Club, Community Service Club, Debate Club, Eco-Leaders, Future Business Leaders of America, Garden Club, Gender Sexuality Alliance, Ich Dien Society, Kindness Club, Magic: The Gathering Club, Manga/Anime, Math Club, Model United Nations, National Honor Society, New England Math League, Peer Counselors, Photography Club, Prefects, Robotics Club, Science Olympiad, Spirit Squad, Student Activities Committee (SAC), Student Equity Team, The Coleman Group, The Transformers, Yearbook
Arts and Music Programs:
Jazz Ensemble, Rock Band, String Ensemble
Recreational Athletic Programs:
Fencing - recreational, Golf - recreational, Strength and Conditioning, Tennis - recreational
College Matriculation
Year: 2015 - 2019
10 Most Popular College Choices (# Enrolled)
UCONN
27
New York University
21
Boston University
16
Marist College
10
Trinity College
9
George Washington University
8
Hobart and William Smith
8
Penn State
8
Connecticut College
7
Fairfield University
7
School Notes
- Founded in 1794, Cheshire Academy is a coed college preparatory boarding and day school for students in grades 9-PG. The historic 104-acre campus is nestled in the bucolic but central town of Cheshire, Conn., just two hours from both Boston and New York City. With 343 students from 14 states and 27 countries, CA takes a flexible and tailored approach, allowing students to combine a variety of academic and extracurricular offerings optimal to their individual needs, strengths, and interests.
- For example, many students choose to stretch their intellectual boundaries by taking some of 36 advanced International Baccalaureate Diploma Programme courses. This internationally respected program offers a global perspective, challenging students to be independent, critical thinkers concerned and involved with the world around them.
- With 27 interscholastic athletic teams, as well as non-competitive offerings and many performing and visual arts options, there`s a program to be experience by all students. CA also offers a unique Art Major program for those who plan to study art or design at the university level.
- Cheshire Academy recognizes that all students learn differently. Through our optional Roxbury Academic Support Program, our trained learning specialists create proactive, independent, competent learners by fostering tools and strategies to meet the rigors of a college preparatory environment and beyond. This proven approach yields thriving students who take responsibility for their academic success.
- Cheshire Academy accreditations: New England Association of Schools and Colleges, National Association of Independent Schools, The Association of Boarding Schools, Connecticut Association of Independet Schools
- Sample of notable school alumni/alumnae:
- JP Morgan - American financier, banker and art collector.
- Roberto C. Goizueta - Former chairman & CEO, Coca-Cola
- Joseph W. Hasel - Voice of the New York Giants
- Rockwell Kent - American artist
- Robert Ludlum - Author best know for The Bourne trilogy.
- Patrick McCaskey - Director, board member, Chicago Bears
- Angela Robinson - State Superior Court judge
- James Van Der Beek - Actor
- Gideon Welles - Secretary of the Navy (Lincoln)
- Talib Kweli - American hip-hop artist
Source: Verified school update
Frequently Asked Questions
How much does Cheshire Academy cost?
Cheshire Academy's tuition is approximately $57,250 for boarding students and $29,850 for day students.
What is the acceptance rate of Cheshire Academy?
The acceptance rate of Cheshire Academy is 45%, which is lower than the boarding school average of 64%.
Who are famous alumni from Cheshire Academy?
Cheshire Academy famous alumni include: JP Morgan, Roberto C. Goizueta, Joseph W. Hasel, Rockwell Kent, Robert Ludlum, Patrick McCaskey, Angela Robinson, James Van Der Beek, Gideon Welles and Talib Kweli.
What sports does Cheshire Academy offer?
Cheshire Academy offers 15 interscholastic sports: Alpine Skiing, Baseball, Basketball, Cross Country, Cross Country Running, Fencing, Football, Golf, Lacrosse, Soccer, Softball, Tennis, Track, Track and Field and Volleyball.
What is Cheshire Academy's ranking?
Cheshire Academy ranks among the top 20 boarding schools for High # of AP/advanced courses offered and Oldest founding date.
When is the application deadline for Cheshire Academy?
The application deadline for Cheshire Academy is Feb. 1 / rolling (applications are due on Feb. 1 but additional applications are reviewed year-round as space permits ).
Alumni Reviews Review School
Review
Description
The Academy stands out in many ways such as how their is always active efforts to bring their immensely diverse community together and from person experience they have found great success. The school stresses the. . .
Was the perfect place for me at the time. Small classroom size suited my needs and forced me to get involved in the curriculum. Required study time at night helped me to develop good study. . .
My family's relationship with Cheshire predates my brother's and my attendance there; our grandfather was a student at the Academy in the 1940s. The family came back to the school because of the summer program. . .
Show more reviews (2 reviews)
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