Private School Review - Established 2003

Cheshire Academy

10 Main St Cheshire, CT 06410
Tel: (203) 439-7250
cheshireacademy.org

Quick Facts (2026-27)

  • Top Ranked CT School
  • Grades: 9-12
  • Enrollment: 369 students
  • Acceptance rate: 63%
  • Average class size: 10 students
  • Application Deadline: Feb. 1 / rolling
  • Source: ✓Verified school update
Cheshire Academy Photo #1 - 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.
Cheshire Academy Photo #2 - 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 #3 - Bowden Hall, completed in 1796, is the oldest schoolhouse in continuous use in the state of Connecticut. Cheshire Academy was founded in 1794 and is the 10th oldest boarding school in the US.
Cheshire Academy Photo #4 - 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 #5 - 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 #6 - Cheshire Academy is home to students from over 30 different countries who chose the Academy because of our reputation as one of the best private schools in the United States. The tradition of enrolling international students at Cheshire Academy dates back to 1850, making this school among the first to enroll students from other countries.
Cheshire Academy Photo #7 - 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 footpaths that wind around campus. The Academy is a tight-knit and dynamic environment that offers a community rich in diversity.
Cheshire Academy Photo #8 - Many students come to Cheshire Academy knowing they love the arts; others discover their passion while attending. Students planning to pursue Art & Design at the university level can take advantage of our year-long Art Major Program.
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 - With 69% of faculty with advanced degrees, an average class size of 10 and a 6:1 student:teacher ratio, CA believes in small classrooms with expert teachers who empower students to take control of their learning.
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About the School

  • Founded in 1794, Cheshire Academy is a coeducational college-preparatory boarding and day school for grades 9-12 and postgraduate.
  • With 368 students from 11 states and 21 countries, Cheshire Academy takes a tailored approach, providing students with a wide variety of academic and extracurricular offerings that are optimal to their individual needs, strengths, and interests.
  • Located in Cheshire, CT, our 104-acre campus rests in a quintessential and safe New England community conveniently located between New York and Boston.
  • CA's supportive, one-to-one college counseling program begins early on, resulting in commitments to some of the country's most competitive colleges and universities.
  • With a wide range of programming, CA offers the world-renowned International Baccalaureate, Roxbury Academic Support, and unique, signature Art and Music Major programs.
  • CA is home to 20+ athletics teams, with nearly 40% of student-athletes in the Class of 2023 going on to play at the collegiate level.

Quick Facts (2026-27)

  • Top Ranked CT School
  • Grades: 9-12
  • Enrollment: 369 students
  • Acceptance rate: 63%
  • Average class size: 10 students
  • Application Deadline: Feb. 1 / rolling
  • Source: ✓Verified school update

School Rankings

Cheshire Academy ranks among the top 20% of private schools in Connecticut for:

Category
Attribute
Student Body
Largest student body
Extra-curric.
Most extracurriculars offered
School History
Oldest founding date

School Facts

School Membership(s)School Assoc.
Institute for Independent Education
National Association of Independent Schools (NAIS)
National Independent Private Schools Association
The Association of Boarding Schools (TABS)
New England Association of Schools and Colleges
International Baccalaureate (IB) World School
Religious Affiliation
Nonsectarian
Grades Offered
Grades 9-12
Students By Grade

Distribution of Students By Grade

GradeCheshire Academy
977
1094
1197
1290
Ungraded11
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Note: Data may not be displayed on any public-facing website or service that replicates or resembles a school search or review portal without prior written permission. See our Terms of Service.

Offers Post-Graduate Year
Yes
ADD/ADHD Support
Yes
Learning Difference Programs
Yes
Learning Programs Supported
Mild Learning Differences
Year Founded
1794
Colors
White, Blue
School Calendar
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Student Body

Total Students
369 students
Student Body Type
Co-ed
% Students of Color
29%
State avg.: 31%

Academics & Faculty

Total Classroom Teachers
55 teachers
Student-Teacher Ratio
7:1
National avg.: 11:1
% Faculty w/Advanced Degree
69%
Average Class Size
10 students
List of Courses Offered
Link to List of Courses
Advanced Courses
Arts Major ProgramHL1/HL2
IB Biology SL & HL1/HL2IB Chemistry SL1/SL2 & HL1/HL2
IB Computer Science SL1/SL2IB Economics SL1/SL2
IB English Language & Literature HL1/2 & SL1/2IB English Literature HL1/2 & SL1/2
IB Environmental Systems and Society SLIB French ab Initio 1/ab Initio 2
IB French SL1/SL2 & HL1/HL2IB History of the Americas SL1/SL2 & HL1/HL2
IB Lit & Performance SL1/SL2IB Mandarin ab Initio 1/ab Initio 2
IB Mandarin SL1/SL2IB Math SL2/HL2
IB Math Studies SL2IB Mathematics: Analysis and Approach SL1
IB Mathematics: Applications and Interpretation SL1IB Music SL1/SL2 & HL1/HL2
IB Physics SL1/SL2 & HL1/HL2IB Spanish SL1/SL2 & HL1/HL2
IB Sports/Exercise/Health Science SLIB Theater SL1/SL2
IB Theory of Knowledge Y1/Y2IB Visual Arts SL1/SL2 & HL1/HL2
Average SAT score
1200
(Out of 1600)
Average ACT score
25
(Out of 36)
Matriculation DataMatric. Data
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Classroom Dress Code
Casual
Mon, Tue, Thur: Academic Dress; Wed CA Spirit Day; Friday: Formal Dress

Tuition & Acceptance Rate

Admission Deadline
Feb. 1 / rolling
Tuition Notes
7-Day Boarding: $62,475 Day: $32,498
% on Financial Aid
49%
Average Financial Aid Grant
$25,573
Acceptance Rate
63%
National avg.: 82%
Admissions Director
Rebecca Brooks
Admissions Associate
Brianna Zegzdryn
Application URL
Online Application
Endowment Size
$13 million

Extracurriculars

Total ExtracurricularsTotal Extra-curric.
24 extracurriculars
ExtracurricularsExtra-curric.
Club or Organization:
Admission Ambassadors (Tour Guides)Art Club
Chess ClubCommunity Service
Digital Photography ClubEco-Leaders
Garden ClubIch Dien Society
International Student SocietyModel UN
National Honor SocietyNew England Math League
Peer CounselorsSchool Newspaper
Science OlympiadThe Gay/Straight Alliance
Yearbook


Arts and Music Programs:
Art Major ProgramDrama
Jazz Ensemble/Rock BandString Ensemble


Recreational Athletic Programs:
FitnessSnowsports Club
Yoga

School Notes

  • School Mascot: Wildcats
  • Founded in 1794, Cheshire Academy is a college preparatory boarding and day school for students in grades 9-12 and postgraduate. The historic 104-acre campus is nestled in the bucolic but central town of Cheshire, Connecticut, just two hours from both Boston and New York. CA takes a flexible and tailored approach, so students can 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 one of 36 advancedInternational BaccalaureateDiploma Programmecourses. 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, non-competitive offerings, many performing and visual arts options, there's a passion to be uncovered for all students. CA also offers unique Art Major and Music Major programs for those who plan to continue on to an arts or music program at the university level.Cheshire Academy recognizes that all students learn differently. Through our optional Roxbury Academic Support Program, our dedicated staff of masters-level instructors creates 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

What schools are Cheshire Academy often compared to?
Cheshire Academy is often viewed alongside schools like Hamden Hall Country Day School by visitors of our site.
What is the acceptance rate of Cheshire Academy?
The acceptance rate of Cheshire Academy is 63%, which is lower than the national average of 71%.
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 14 interscholastic sports: Alpine Skiing, Baseball, Basketball, Cross Country, E-sports, Fencing, Football, Golf, Lacrosse, Soccer, Softball, Tennis, Track and Field and Volleyball.
What is Cheshire Academy's ranking?
Cheshire Academy ranks among the top 20% of private schools in Connecticut for: Largest student body, Most extracurriculars 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 ).
In what neighborhood is Cheshire Academy located?
Cheshire Academy is located in the Cheshire Village neighborhood of Cheshire, CT. There are 1 other private schools located in Cheshire Village.

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Did You Know?

The average private school tuition in New Haven County, CT is $19,109 for elementary schools and $29,229 for high schools (read more about average private school tuition across the country).
The average acceptance rate in New Haven County, CT is 73% (read more about average acceptance rates across the country).

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