Cheshire Academy (2026 Profile)

5.00 (5 reviews)

Tel: (203) 439-7250

10 Main Street
Cheshire, CT 06410

cheshireacademy.org

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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 Facts (2026)

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 307 schools) for:

School Overview

| 2025 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

1909

Campus Size

100 acres

125 acres

School Calendar

View School Calendar

School Motto

From Here to Anywhere

Student Body

Enrollment

343 students

300 students

% Students of Color

34%

25%

% International Students

30%

20%

% Students Boarding

52%

70%

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

Academic Profile

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%

70%

Summer Program Offered

Yes

Summer Program Details

View Summer Program Details

# of AP / Advanced Courses Offered

Courses

AP Calculus I-ABAP Music Theory

AP PsychologyAP Statistics

Arts Major ProgramIB Biology SL & HL1/HL2

IB Chemistry SL1/SL2 & HL1/HL2IB Computer Science SL1/SL2

IB Economics SL1/SL2IB English Language & Literature HL1/2 & SL1/2

IB English Literature HL1/2 & SL1/2IB Environmental Systems and Society SL

IB French ab Initio 1/ab Initio 2IB French SL1/SL2 & HL1/HL2

IB History of the Americas SL1/SL2 & HL1/HL2IB Lit & Performance SL1/SL2

IB Mandarin ab Initio 1/ab Initio 2IB Mandarin SL1/SL2

IB Math SL2/HL2IB Math Studies SL2

IB Mathematics: Analysis and Approach SL1IB Mathematics: Applications and Interpretation SL1

IB Music SL1/SL2 & HL1/HL2IB Physics SL1/SL2 & HL1/HL2

IB Spanish SL1/SL2 & HL1/HL2IB Sports/Exercise/Health Science SL

IB Theater SL1/SL2, HL1/HL2IB Theory of Knowledge Y1/Y2

IB Visual Arts SL1/SL2 & HL1/HL2

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Tuition & Financial Aid

Endowment Size

$16.3 million

$25 million

Yearly Tuition
(Boarding Students)

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

$59,900

Yearly Tuition
(Day Students)

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

$33,500

Tuition international students

$67,250

$53,975

Yearly Tuition
(5 Day Boarding)

$55,250

$44,000

% Students on Financial Aid

43%

40%

Avg. Financial Aid Grant

$23,750

$25,000

Merit Scholarships Offered

Yes

Admissions

Application Deadline

Feb. 1 / rolling

Jan. 15

Acceptance Rate

45%

58%

Director of Admissions

Rebecca Brooks

Application URL

Online Application

Sports

# Interscholastic Sports Offered

Sports

Alpine SkiingBaseball

BasketballCross Country

Cross Country RunningFencing

Track and FieldUltimate Frisbee

Volleyball

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Colors

White, Blue

School Mascot

The Cats

Extracurriculars

Total Extracurricular Organizations

Extracurriculars

Club or Organization:

Admission AmbassadorsAstronomy Club

Black Student UnionCandy Club

Ceramics ClubChess Club

Community Service ClubDebate Club

DECADiscussion Club

Eco-LeadersFilm Making Club

Finance ClubGarden Club

Gay/Straight AllianceIch Dien Society

Juxtaposition Literary MagazineKindness Club

Laptop OrchestraLe French Club

Magic: The Gathering ClubMath Club

Media: Good Day CAModel United Nations

National Honor SocietyNew England Math League

Newspaper: Paw PrintPeer Counselors

PrefectsRobotics Club

Science OlympiadSpirit Squad

Student Activities Committee (SAC)Student Equity Team

The Coleman GroupYearbook

Show More (20)Hide

Arts and Music Programs:

Jazz EnsembleRock Band

String Ensemble

Recreational Athletic Programs:

Fencing - recreationalGolf - recreational

Strength and ConditioningTennis - recreational

College Matriculation

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

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.
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

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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 19 interscholastic sports: Alpine Skiing, Baseball, Basketball, Cross Country, Cross Country Running, Fencing, Field Hockey, Football, Golf, Lacrosse, Snowboarding, Soccer, Softball, Swimming, Tennis, Track, Track and Field, Ultimate Frisbee and Volleyball.

Does Cheshire Academy offer a summer program?

Yes, Cheshire Academy offers a summer program. Visit their summer school page for more information.

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)

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