Cheshire Academy

5.00 5 1 (5 reviews)
10 Main Street
Cheshire, CT 06410
Cheshire Academy Photo #1 - Bowden Hall, completed in 1796, is the oldest schoolhouse in continuous use in the state of Connecticut
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 - 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 #4 - 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 #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 - 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 #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 - With 42 faculty with advanced degrees and a 6:1 student:teacher ratio, CA believes in small classrooms with expert teachers who empower students to take control of their learning.
Cheshire Academy Photo #9 - 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 #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 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 362 students from 15 states and 30 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 20 Placements

Cheshire Academy is listed among the top 20 boarding schools (out of 323 schools) for:

Definition of Terms
 | 2019 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 Founded17941910
Campus Size104 acres105 acres

Student Body

Enrollment362 students313 students
% International Students
% Students Boarding
Average SAT Score1180* National Avg. »View
SAT range (25th-75th percentile)1060 - 1300-
Average ACT score25*National Avg. » View
Offers Post-Grad YearYesNo

Academics and Faculty

Saturday ClassesNoNo
Classroom Dress CodeCasual
(Dress is business casual Monday, Tuesday, and Thursday, with casual Wednesdays and formal Fridays.)
Average Class Size12 students12
*National School Avg. » 20
Teacher : Student Ratio1:61:7
# of AP / Advanced Courses Offered618
Number of IB Courses Offered20-
ESL Courses OfferedYesYes
% Faculty with Advanced Degree
Summer Program OfferedNoYes


Endowment Size$11 million$20 million
Yearly Tuition
(Boarding Students)
Yearly Tuition
(Day Students)
% Students on Financial Aid
Avg. Financial Aid Grant$23,500$25,000
Merit Scholarships OfferedYesNo


Application DeadlineFeb. 1 / rollingJan. 15
Accepts Standardized ApplicationYesNo
SSAT RequiredYesYes
Acceptance Rate
Director of AdmissionsSara Lynn Leavenworth
Associate Director of AdmissionsDevin Worthington

Course Listings

List of Courses OfferedLink to List of Courses

AP / Advanced Courses

# of AP / Advanced Courses Offered618
CoursesAP Calculus I-AB, AP Literature & Composition, AP Music Theory, AP Psychology, AP Statistics, 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 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 SL1/SL2 & HL1/HL2, IB Music SL1/SL2 & HL1/HL2, IB Physics SL1/SL2, 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 Offered1916
SportsAlpine 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, Volleyball


Total Extracurricular Organizations3223
ExtracurricularsClub or Organization:
Admission Ambassadors, Art Club, Candy Club, Captains Council, Chess Club, Citizenship Committee, Community Service Club, Connecticut Youth Forum, Digital Photography Club, Eco-Leaders, Ich Dien Society, Juxtaposition Literary Magazine, Marketing & Communications Interns, Mathematical Modeling Team, Model United Nations, National Honor Society, New England Math League, Peer Counselors, Prefects, The Coleman Group, The Gay/Straight Alliance, The International Student Society, The New Review Student Newspaper, Yearbook, Young Entrepreneurs Club

Arts and Music Programs:
Cheshire Academy Through Sound, Jazz Ensemble, Piano Master Class, Rock Band, String Ensemble, The Varsity Players Theater Troupe

Recreational Athletic Programs:
Snowports Club

College Matriculation

Year: 201710 Most Popular College Choices  (# Enrolled)
Boston University5
New York University5
Boston College4
Hobart and William Smith College3
University of California, San Diego3
Fordham University2
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 362 students from 13 states and 29 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 20 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, 10 non-competitive offerings, 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:

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