Cheshire Academy

5.00 5 1 (4 reviews)
Tel: 2034397250
10 Main Street
Cheshire, CT 06410
  • Cheshire Academy is a boarding school in Connecticut that challenges students in grades 9-12 and post graduate to discover and hone their unique talents.
  • This college preparatory school offers personalized learning opportunities like the Roxbury Academic Support Program and the IB Program.
  • Artists can benefit from the Art Major program, while high school athletes can benefit from competitive athletics.
  • Overall, students at the private school are encouraged to 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 2016
    5 Stars   5/31/2017
    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. . .

  • Class of 2005
    5 Stars   6/22/2014
    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. . .

  • Class of 1999
    5 Stars   6/24/2014
    Guilford College
    One aspect of Cheshire Academy that I liked in particular was the diverse and inclusive feeling of the school. When I attended, CA had a large proportion of students from overseas, which made for interesting. . .

  • Class of 1980
    5 Stars   8/4/2017
    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. . .
  • Show more reviews (-1 reviews)

Top 20 Placements

Listed among the top 20 boarding schools (out of 320 schools) for:

Definition of Terms 
2018 School Data
Cheshire AcademyBoarding School Avg.
School FocusCollege PrepCollege Preparatory
Grades Offered9-12, PG7-12
School TypeCo-edCo-ed
ADD/ADHD SupportYesYes
Supports Learning Differences (LD)YesYes
Religious AffiliationNon-denominationalNon-denominational
Year Founded17941909
Campus Size104 acres105 acres

Student Body

Enrollment420 students300 students
% Students Boarding
Average SAT Score1130* National Avg. »View
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 Size9 students12
*National School Avg. » 20
Teacher : Student Ratio1:61:7
# of AP / Advanced Courses Offered617
Number of IB Courses Offered25-
ESL Courses OfferedYesYes
% Faculty with Advanced Degree
Summer Program OfferedYesYes


Yearly Tuition
(Boarding Students)
Yearly Tuition
(Day Students)
% Students on Financial Aid
Avg. Financial Aid Grant22734$23,000
Merit Scholarships OfferedYesNo


Application DeadlineFeb. 10 / rollingJan. 15
Accepts Standardized ApplicationYesNo
SSAT RequiredYesYes
Acceptance Rate
Director of AdmissionsNathan Wright
Associate Director of AdmissionsDevin Worthington

Course Listings

List of Courses OfferedLink to List of Courses

AP / Advanced Courses

# of AP / Advanced Courses Offered617
CoursesAP American Government, AP Calculus I-AB, AP Language & Composition, AP Literature & Composition, AP Music Theory, AP Psychology, AP Statistics


# Interscholastic Sports Offered1915
SportsAlpine Skiing, Baseball, Basketball, Cross Country, Dance, Fencing, Field Hockey, Football, Golf, Lacrosse, Snowboarding, Soccer, Softball, Swimming, Tennis, Track and Field, Ultimate Frisbee, Volleyball, Wrestling


Total Extracurricular Organizations2224
ExtracurricularsClub or Organization:
Campus, Chess Club, Community, Computer Club, Craft, Dramatics, Gay Straight Alliance (GSA), Key, Math, National, Peer, Proctors, Prom, Student

Arts and Music Programs:
Chamber, Drama Club, Horizons, Jazz Club

Recreational Athletic Programs:
Martial, Ropes, Ski, Yearbook

College Matriculation

Year: 201710 Most Popular College Choices  (# Enrolled)
Boston University5
New York University5
Boston College4
Hobart and William Smith College3
Link to Matriculation Data

School Notes

  • The Student-Centered School, Cheshire Academy is a community within a community, close to large cities, yet suburban enough that students feel comfortable on- and off-campus. What discoveries await a student here? There are as many answers to that question as there are students, because education that inspires the individual is our way of life. Students, teachers, coaches, and parents combine their diverse talents to create a learning and living environment that honors the differences in all of us. Our history includes women and men who changed the course of world events because they stood up for who they are, and we`re proud they learned to do that here. While our past makes us one of the nation`s oldest schools, our progressive curriculum encourages intellectual and ethical maturity for today`s global society.
  • Academics & College Prep: Cheshire stresses strong, informed college preparation. We offer the International Baccalaureate Diploma Programme, a range of honors classes, AP courses, electives, and independent studies. Academic support, including a writing center and math lab, rounds out our curriculum. A full-time college counseling team guides students through their college search process, and more than 150 college representatives visit campus each year. 2015 college acceptances included Brown, Bates College, Bowdoin College, Boston College, Cornell, Duke, Tufts, New York University, Johns Hopkins, Vanderbilt University, University of Michigan, and Bucknell.
  • Athletics & Afternoon Programs: The tradition of athletics is integral to the life of Cheshire Academy. With programs including baseball, basketball, cross country, fencing, field hockey, football, golf, ice hockey, lacrosse, soccer, softball, swimming, tennis, track, ultimate Frisbee, volleyball, and wrestling, each student is encouraged to participate for a minimum of one season, although many choose to play all three. For those who want to explore a new sport, the beginning and junior varsity teams provide a chance to acquire basic skills, make new friends, and learn about sportsmanship. Cheshire Academy`s other afternoon programs introduce new interests and life-long passions that emphasize teamwork, goal setting, and self-confidence. Our community has produced a wide range of internationally recognized athletes, musicians, actors, novelists, and playwrights.
  • Extracurricular Activities: Extracurricular activities are as varied as student interests, often organized in response to student requests. The Proctors, Student Council, Peer Counselors, and the National Honor Society provide student leadership. Our many other organizations include the Diversity Club, Key Club, Earth Club, Chess Club, Model U.N., and two computer clubs. A literary magazine and new multi-media clubs provide practical experience in writing, editing, photography, and digital imaging.
  • Campus Life: Learning occurs not only in classrooms but also in halls and dormitories. A powerful connection is created when teachers also serve as dorm parents and advisors. Programs like the Citizenship Committee are fundamental to who we are as a school and a community. Each program adds to our authentic, whole-learning environment, and students are able to voice their opinions about the activities that interest them. To follow what our students are currently up to, find us on facebook!
  • Financial Assistance: Cheshire Academy annually awards $4.1 million in financial assistance. In addition, we award a four-year scholarship to a town resident, a three-year scholarship to an incoming sixth grader, and a scholarship from the Goizueta Foundation for a candidate of Latin background.
  • Admission: There is much more to learn about us! We look forward to showing you our wonderful community. To arrange a tour, please contact the admission office at 203-439-7250.
  • LD types supported: Mild Learning Differences
  • School 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:
    • Fred Friendly - Former president, CBS News
    • Roberto C. Goizueta - Former chairman & CEO, Coca-Cola
    • Joseph W. Hasel - Voice of the New York Giants
    • Rockwell Kent - Artist
    • Robert Ludlum - Author
    • J.P. Morgan - Industrialist
    • Angela Robinson - State Superior Court judge
    • James Van Der Beek - Actor
    • Gideon Welles - Secretary of the Navy (Lincoln)
    • Patrick McCaskey - Director, board member, Chicago Bears
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