Cheshire Academy
Quick Stats (2023)
- Grades: (Boarding) 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 294 schools) for:
School Overview
Student Body
Academics and Faculty
Dress is "academic dress" (one step above casual) Monday, Tuesday, and Thursday, with casual Wednesdays (CA spirit wear) and formal Fridays (a historic tradition).
Tuition Cost
(Boarding Students)
(Reduced by 10% for 2022-23.)
(Day Students)
(Reduced by nearly one third for 2022-23.)
(5 Day Boarding)
Acceptance Rate
AP / Advanced Courses
Sports
Extracurriculars
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
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
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 58%.
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
Recent Articles


