Cheshire Academy (2025 Profile)

5.00 (5 reviews)

Tel: (203) 439-7250

10 Main Street
Cheshire, CT 06410

cheshireacademy.org

REQUEST INFO

SAVE SCHOOL

Cheshire Academy Photo #1 - Our 104 acre (0.42 sq km) campus is in the center of the quiet, beautiful Town of Cheshire, CT. Though just a two hour drive to both Boston and New York, Cheshire is a quiet small town where students are in walking distance of a few area shops and cafes.

Cheshire Academy Photo #2 - A diverse student body, unlimited variety in student clubs and activities, a unique combination of 7-day and 5-day boarding with a great day student population, all add up to a high school experience in which every student will belong, enjoy, and excel.

Cheshire Academy Photo #3 - With the majority of teachers living on campus, 73% of faculty holding advanced degrees, an average class size of 10, and a 6:1 student:teacher ratio, CA features small classes with expert teachers who are fully engaged with and support every student, guiding them on their individual path to college and beyond.

Cheshire Academy Photo #4 - Cheshire Academy is home to students from over 20 countries who chose CA because of our reputation as one of the best international private schools in the United States, among the most diverse in the region.

Cheshire Academy Photo #5 - The Cheshire Academy experience is full and active; living and learning takes place not only in the classroom, but also in the art studios, dormitories, dining commons, on the athletic fields, and even on the patios and footpaths around campus. The Academy is a tight-knit and dynamic environment that offers a community rich in diversity.

Cheshire Academy Photo #6 - Our academic process begins with what students know and want to know, and develops active learners who reflect on their growth and the implications of their learning. Cheshire Academy students grow increasingly capable of independently observing, questioning, explaining, interpreting, and analyzing the world.

Cheshire Academy Photo #7 - CA offers 7-day and 5-day boarding. Living on campus is the one of the best ways to prepare for life at college-through a safe environment to explore your independence and take on greater responsibility. Students enjoy a full-service dining facility, fitness center, study areas, student center, and the convenience of restaurants and grocery stores within walking distance.

Cheshire Academy Photo #8 - We offer a variety of athletic programs each season. The Academy teaches student-athletes the skills and knowledge necessary to learn the sport while also producing championship-winning teams.

Cheshire Academy Photo #9 - CA believes all students can benefit from music education, from beginners to students planning a career in music. Students of music at CA develop tenacity, patience, focus, and confidence, and also have many opportunities to display leadership in several student-led ensembles. Advanced students can take private lessons, audition for all-state festivals, and study AP Music Theory and IB Music.

Cheshire Academy Photo #10 - Character development has long been a priority at Cheshire Academy. The Eight Pillars of Bowden are the ways in which we demonstrate our core values and basic beliefs: Respect, Responsibility, Caring, Civility, Citizenship, Morality, Fairness and Trustworthiness.

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 280 schools) for:

School Overview

| 2024 School Data

Cheshire Academy

Boarding School Avg.

School Focus

College Preparatory

Grades Offered

9-12, PG

9-12

School Type

Co-ed

ADD/ADHD Support

Yes

Supports Learning Differences (LD)

Yes

Religious Affiliation

Non-denominational

Year Founded

1794

1907

Campus Size

104 acres

125 acres

Colors

White, Blue

School Calendar

View School Calendar

Student Body

Enrollment

343 students

319 students

% Students of Color

34%

27%

% International Students

27%

21%

% Students Boarding

52%

67%

Average SAT Score

1200
(Out of 1600)

* National Avg. »View

SAT range (25th-75th percentile)

1070 - 1390

Average ACT score

25
(Out of 36)

*National Avg. »View

Offers Post-Grad Year

Yes

Academics and Faculty

Saturday Classes

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).

Casual

Average Class Size

10 students

* National Avg. »18

Student : Teacher Ratio

6:1

7:1

# of AP / Advanced Courses Offered

Number of IB Courses Offered

ESL Courses Offered

Yes

% Faculty with Advanced Degree

73%

72%

Summer Program Offered

Yes

Tuition Cost

Endowment Size

$16.3 million

$30 million

Yearly Tuition
(Boarding Students)

$57,250
(Reduced by 10% for 2022-23.)

$66,900

Yearly Tuition
(Day Students)

$29,850
(Reduced by nearly one third for 2022-23.)

$35,500

Tuition international students

$67,250

$58,300

Yearly Tuition
(5 Day Boarding)

$55,250

$49,300

% Students on Financial Aid

43%

40%

Avg. Financial Aid Grant

$23,971

$25,000

Merit Scholarships Offered

Yes

Admissions

Application Deadline

Feb. 1 / rolling

Jan. 15

Acceptance Rate

45%

64%

Director of Admissions

Rebecca Brooks

Application URL

Online Application

AP / Advanced Courses

# of AP / Advanced Courses Offered

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

Sports

Alpine Skiing, Baseball, Basketball, Cross Country, Cross Country Running, Fencing, Football, Golf, Lacrosse, Soccer, Softball, Tennis, Track, Track and Field, Volleyball

Extracurriculars

Total Extracurricular Organizations

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

College Matriculation

Year: 2015 - 2019

10 Most Popular College Choices (# Enrolled)

UCONN

New York University

Boston University

Marist College

Trinity College

George Washington University

Hobart and William Smith

Penn State

Connecticut College

Fairfield University

View Matriculation Data

School Notes

School Motto: From Here to Anywhere
School Mascot: The Cats
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

REQUEST FREE INFORMATION

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

Cheshire Academy Alumni #1
Class of 2017
5.008/5/2019
Hobart

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. . .

Cheshire Academy Alumni #2
Class of 1980
5.008/4/2017
Fordham University

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. . .

Cheshire Academy Alumni #3
Class of 2016
5.005/31/2017
Syracuse University

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)

Recent Articles

June 10, 2025

Wait A Year Before Going to College

This article explores the benefits of taking a gap year or a postgraduate year before attending college. It discusses how these options can provide students with additional time to refine their academic skills, gain practical experience, and mature before entering higher education. The article highlights the advantages of both paths, including improved college readiness and enhanced personal growth.