Cheshire Academy

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.
Founded in 1794, Cheshire Academy is a boarding and day school for students in grades 9-12 plus PostGraduate (PG).
The historic 104-acre (0.42 sq km) campus is nestled in the bucolic but central town of Cheshire, CT, just two hours drive from both Boston and New York.
With approximately 344 students from 19 states and 31 countries, the Academy takes a exible and tailored approach, allowing students to combine a variety of academic and extracurricular oerings optimal to their individual needs, strengths, and interests.

Quick Stats (2021)

  • Top Ranked CT School
  • Grades: 9-12
  • Students: 344 students
  • Acceptance rate: 53%
  • Average class size: 10 students
  • Application Deadline: Feb. 1 / rolling

Top Placements

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

School History

School Overview

Religious Affiliation
Grades Offered
Grades 9-12
Offers Post-Graduate Year
ADD/ADHD Support
Learning Difference Programs
Learning Programs Supported
Mild Learning Differences
Year Founded
Summer School Offered
Summer Program Cost
Summer Program Cost Notes
Varies based on program
Summer Program Details

Student Body

Total Students
344 students
Student Body Type
% Students of Color
State avg.: 27%
Students by Grade
Cheshire Academy Student By Grade

Academics and Faculty

Total Classroom Teachers
53 teachers
Student : Teacher Ratio
National avg.: 13:1
% Faculty w/Advanced Degree
Average Class Size
10 students
Number of AP Courses
4 courses
List of Courses Offered
Advanced Courses
AP Calculus I-AB, AP Music Theory, AP Psychology, AP Statistics, Arts Major Program, HL1/HL2, 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, IB Theory of Knowledge Y1/Y2, IB Visual Arts SL1/SL2 & HL1/HL2
Average SAT score
Average ACT score
Matriculation DataMatric. Data
Classroom Dress Code
(Mon, Tue, Thur: Academic Dress; Wed CA Spirit Day; Friday: Formal Dress)

Finances and Admission

Admission Deadline
Feb. 1 / rolling
Tuition Notes
7 Day Boarding: $63,600 5 Day Boarding: $55,375 Day: $42,320
% on Financial Aid
Average Financial Aid Grant
Acceptance Rate
National avg.: 85%
Admissions Director
Sara Lynn Leavenworth
Admissions Associate
Cara Jordan
Endowment Size
$16.3 million



Total ExtracurricularsTotal Extra-curric.
30 extracurriculars
Club or Organization:
Admission Ambassadors (Tour Guides), Art Club, Candy Club, Chess Club, Community Service, Digital Photography Club, Eco-Leaders, Garden Club, Ich Dien Society, International Student Society, Literary Magazine, Marketing & Communication Interns, Model UN, National Honor Society, New England Math League, Peer Counselors, School Newspaper, Science Olympiad, The Gay/Straight Alliance, Yearbook, Young Entrepreneurs Club

Arts and Music Programs:
Art Major Program, Dance, Drama, Jazz Ensemble/Rock Band, Piano Master Class, String Ensemble

Recreational Athletic Programs:
Fitness, Snowsports Club, Yoga

School Notes

  • Founded in 1794, Cheshire Academy is a 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, CT, just two hours from both Boston and New York.
  • With approximately 344 students from 19 states and 31 countries, the Academy 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 one of 45 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 just over 20 interscholastic athletic teams, as well as non-competitive offerings and many performing and visual arts options, there`s a passion to be uncovered for all students.
  • The Academy also offers a unique Art Major program for those who plan to continue on to an arts or design program 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.
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Quick Stats (2021)

  • Top Ranked CT School
  • Grades: 9-12
  • Students: 344 students
  • Acceptance rate: 53%
  • Average class size: 10 students
  • Application Deadline: Feb. 1 / rolling

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Did You Know?

The average private school tuition in New Haven County, CT is $18,089 for elementary schools and $32,176 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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