Cheshire Academy (2026-27 Profile)

REQUEST INFO

SAVE SCHOOL

About the School

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 (26-27)

Grades: 9-12, PG
Enrollment: 376 students
Yearly Tuition (Boarding Students): $69,400
Yearly Tuition (Day Students): $37,425
Acceptance rate: 40%
Average class size: 10 students
Application Deadline: Jan. 15 / rolling
Source: Verified school update

Top Rankings

Cheshire Academy ranks among the top 20 boarding schools (out of 271 schools) for:

School Overview

2026 School Data

Cheshire Academy

Boarding School Avg.

School Focus

College Preparatory

Grades Offered

9-12, PG

8-12

School Type

Co-ed

Yes

Religious Affiliation

Non-denominational

Year Founded

1794

1907

Campus Size

104 acres

125 acres

School Motto

From Here to Anywhere

Student Body

Enrollment

376 students

319 students

34%

27%

24%

21%

% Students Boarding

52%

65%

1200
(Out of 1600)

* National Avg. »View

1070 - 1390

Average ACT score

25
(Out of 36)

*National Avg. »View

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

Yes

Summer Program Offered

Yes

Accreditations

Connecticut Association of Independent Schools (CAIS-CT)
National Association of Independent Schools (NAIS)
New England Association of Schools and Colleges (NEASC)
The Association of Boarding Schools (TABS)

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

Show More (13)Hide

Tuition & Financial Aid

Endowment Size

$16.3 million

$30 million

Yearly Tuition
(Boarding Students)

$69,400

$71,420

Yearly Tuition
(Day Students)

$37,425

$40,000

Tuition international students

$80,400

$58,650

Merit Scholarships Offered

Yes

Weekly

Request Information

Step 1 of 2

I am a:

Parent

Student

Name of parent:

Student first name:

Student last name:

Email:

Phone:

Student is:

Male

Female

Currently in grade:

Seeking entry for grade:

Target start date:

Step 2 of 2

Home address:

City:

Country:

State:

Zip: (enter "N/A" if not applicable)

Save this data and create your user profile. Create your own user account so you don't have to re-type your user data each time you request information. You'll also be able to track your information requests, get reminded of application dates, and more!

Username:

Password:

Admissions

Application Deadline

Jan. 15 / rolling

Jan. 15

Acceptance Rate

40%

64%

Director of Admissions

Melissa Terrio

Application URL

Online Application

Sports

# Interscholastic Sports Offered

Sports

Alpine SkiingBaseball

BasketballCross Country

Cross Country RunningFencing

Colors

White, Blue

School Mascot

The Cats

Extracurriculars

Total Extracurricular Organizations

Extracurriculars

Club or Organization:

Admission AmbassadorsAstronomy Club

Black Girl CoalitionBlack Student Union

Candy ClubCeramics Club

Chess ClubCommunity Service Club

Debate ClubEco-Leaders

Future Business Leaders of AmericaGarden Club

Gender Sexuality AllianceIch Dien Society

Kindness ClubMagic: The Gathering Club

Manga/AnimeMath Club

Model United NationsNational Honor Society

New England Math LeaguePeer Counselors

Photography ClubPrefects

Robotics ClubScience Olympiad

Spirit SquadStudent Activities Committee (SAC)

Student Equity TeamThe Coleman Group

The TransformersYearbook

Show More (16)Hide

Arts and Music Programs:

Jazz EnsembleRock Band

String Ensemble

Recreational Athletic Programs:

Fencing - recreationalGolf - recreational

Strength and ConditioningTennis - recreational

College Matriculation

College Acceptance Rate

100%

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

REQUEST FREE INFORMATION

Frequently Asked Questions

How much does Cheshire Academy cost?

Cheshire Academy's tuition is approximately $69,400 for boarding students and $37,425 for day students.

What is the acceptance rate of Cheshire Academy?

The acceptance rate of Cheshire Academy is 40%, 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 Oldest founding date.

When is the application deadline for Cheshire Academy?

The application deadline for Cheshire Academy 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

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

October 20, 2026

AI Isn’t the Problem: Teaching Students to Use It Well

Is AI in the classroom a shortcut or a stepping stone to deeper learning? Explore how teaching AI literacy rather than banning it - can build critical thinking, strengthen language skills, and preserve human connection in education.

October 19, 2026

What If Your Child's Boarding School Advisor Leaves?

Learn what happens when your child's boarding school advisor leaves midyear, including reassignment, academic support, parent communication, student relationships, and practical steps families can take to ensure continuity.

October 19, 2026

What Parents Are Told About Boarding School Dorm Incidents

Discover what boarding schools tell parents about dorm incidents, including bullying, injuries, disciplinary problems, notification policies, privacy protections, reporting timelines, and questions families should ask before choosing a residential school.