Cheshire Academy

5.00 (5 reviews)
10 Main Street
Cheshire, CT 06410
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 #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. Founded in 1794, Cheshire Academy 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 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.
CA offers personalized learning opportunities like the Roxbury Academic Support Program, the International Baccalaureate (IB) Program and Art Major Program.
Cheshire Academy has over 20 sports 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.

Alumni Reviews
  Review School

  • Review Description

  • Class of 2017
    5 Stars  
    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. . .

  • Class of 2016
    5 Stars  
    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. . .

  • Class of 2005
    5 Stars  
    Johnson & Wales University
    I lived in a house that was converted into a dorm, with the dorm parent living on the 1st floor, and five students living on the 2nd floor. Because the dorm had so few. . .
  • Show more reviews (2 reviews)

Top Rankings

Cheshire Academy ranks among the top 20 boarding schools (out of 303 schools) for:

Definition of Terms
 | 2021 School Data
Cheshire AcademyBoarding School Avg.
School FocusCollege PrepCollege Preparatory
Grades Offered9-12, PG5-12
School TypeCo-edCo-ed
ADD/ADHD SupportYesYes
Supports Learning Differences (LD)YesYes
Religious AffiliationNon-denominationalNon-denominational
Year Founded17941907
Campus Size104 acres125 acres

Student Body

Enrollment344 students300 students
% Students of Color
% International Students
% Students Boarding
Average SAT Score1200* National Avg. »View
SAT range (25th-75th percentile)1070 - 1390-
Average ACT score25*National Avg. » View
Offers Post-Grad YearYesNo

Academics and Faculty

Saturday ClassesNoNo
Classroom Dress CodeCasual
(Dress is "academic dress" (one step above casual) Monday, Tuesday, and Thursday, with casual Wednesdays (CA spirit wear) and formal Fridays (a historic tradition).)
Average Class Size10 students12
*National School Avg. » 18
Student : Teacher Ratio6:17:1
# of AP / Advanced Courses Offered4518
Number of IB Courses Offered45-
ESL Courses OfferedYesYes
% Faculty with Advanced Degree
Summer Program OfferedYesYes
Summer Program DetailsLink to Summer Program Details

Tuition Cost

Endowment Size$16.3 million$25 million
Yearly Tuition
(Boarding Students)
Yearly Tuition
(Day Students)
Tuition international students$66,600$54,500
Yearly Tuition
(5 Day Boarding)
Summer Program Cost$1,100
(Cost is per course in summer program. College Counseling Bootcamp available for additional fee.)
% Students on Financial Aid
Avg. Financial Aid Grant$23,971$25,000
Merit Scholarships OfferedYesNo

Acceptance Rate

Application DeadlineFeb. 1 / rollingJan. 15
Accepts Standardized ApplicationNoNo
SSAT RequiredYesYes
Acceptance Rate
Director of AdmissionsSara Lynn Leavenworth

Course Listings

List of Courses OfferedLink to List of Courses

AP / Advanced Courses

# of AP / Advanced Courses Offered4518
CoursesAP 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


# Interscholastic Sports Offered1516
SportsAlpine Skiing, Baseball, Basketball, Cross Country, Cross Country Running, Fencing, Football, Golf, Lacrosse, Soccer, Softball, Tennis, Track, Track and Field, Volleyball


Total Extracurricular Organizations3123
ExtracurricularsClub or Organization:
Admission Ambassadors, CA LEAPS Leadership Club, Candy Club, Ceramics Club, Chess Club, Community Service Club, Debate Club, Discussion Club, Eco-Leaders, Film Making Club, Finance Club, Garden Club, Ich Dien Society, Juxtaposition Literary Magazine, Kindness Club, Laptop Orchestra, Le French Club, Marketing & Communications Interns, Math Club, Model United Nations, National Honor Society, New England Math League, Peer Counselors, Prefects, The Coleman Group, The Gay/Straight Alliance, The Spirit Squad "The Den", Yearbook

Arts and Music Programs:
Jazz Ensemble, Rock Band, String Ensemble

College Matriculation

Year: 2015 - 201910 Most Popular College Choices  (# Enrolled)
New York University21
Boston University16
Marist College10
Trinity College9
George Washington University8
Hobart and William Smith8
Penn State8
Connecticut College7
Fairfield University7
Link to Matriculation Data

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.
  • LD types supported: Mild Learning Differences
  • 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

Profile last updated: 03/03/2021

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