Cheshire Academy - Review #4

Read more details about Cheshire Academy on their 2023 profile page.
Cheshire Academy

About the Author:

Years Attended Boarding School:
Sports and Activities:
I participated in soccer, volleyball, softball, theater/drama, yearbook, the National Honor Society, and probably many more that I cannot recall.
College Enrolled:
Guilford College
Home Town, State:
Cheshire, CT

Reflections and Advice:

1.) What do you think makes your school unique relative to other boarding schools?
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 conversation in the classroom.
2.) What was the best thing that happened to you in boarding school?
Cheshire Academy supported me during those tough high school years and prepared me for a wonderful college experience. I am very grateful to them for this.
3.) What might you have done differently during your boarding school experience?
I did not board, so I don't think I can offer any advice in that regard.
4.) What did you like most about your school?
I love the teachers and staff, and the opportunities afforded me as a part of Cheshire Academy.
5.) Do you have any final words of wisdom for visiting or incoming students to your school?
Because my time at CA was quite a long time ago, I don't think I have any specific places to recommend to them, on campus or otherwise. However, I continue to stay connected to CA and I can tell you that once you are part of the community you never truly leave. I still talk to faculty and staff, who continue to wonder after my success in life and love. That level of caring and dedication is not seen very often.


1.) Describe the academics at your school - what did you like most about it?
The teachers were very dedicated and there was a reasonable amount of curriculum choice offered to students with a particular interest. The teachers were extremely dedicated and highly qualified. I was a smart kid and they pushed me to be better. There was never a question, if I needed help, that a teacher would be there to sit with me after class and go through a particular concept one more time. The classes were so small you had no choice but to come prepared and ready to learn.Twenty years later, I am still connected to many of the teacher and staff of Cheshire Academy.


1.) Describe the athletics at your school - what did you like most about it?
At Cheshire Academy, you had to participate in after school programs but were able to choose what you wanted to do. I am a natural athlete, and enjoyed playing volleyball, softball, and soccer (primarily) during my time at CA. The field house was old but adequate and clean, and the fields nicely maintained. The coaches pushed you to do your very best, and some of my best moments at CA were on the soccer fields. Because everyone was required to participate in after school programs and our school was small, we were competitive but we certainly weren't an "A" level soccer program. They certainly weren't drafting students to play on our teams when I was there, with the exception of basketball. We were very competitive then.I have heard in recent years the football program has become very strong as well, but it did not exist when I attended in the 90s.

Art, Music, and Theatre:

1.) Describe the arts program at your school - what did you like most about it?
I participated in voice lessons and choir and these were excellent.The theatre program went through significant change during my tenure. We had two drama teachers while I was there and the actual theater moved a few times too from one building to another. We put on fairly challenging and some slightly provocative plays and we loved it. Many many wonderful memories.

Extracurricular Opportunities:

1.) Describe the extracurriculars offered at your school - what did you like most about it?
There were so many extracurricular activities to choose from-too many to mention. The staff is open and flexible to build clubs based on student interest as well. A strong point of the school!

Dorm Life:

1.) Describe the dorm life in your school - what did you like most about it?
I did not dorm at CA-I was a day student.


1.) Describe the dining arrangements at your school.
I ate lunch in the cafeteria and also worked there to earn a little extra money during my high school years. The staff were caring and the food was good cafeteria food. They made many adjustments and accommodations for the particular diets of the student body because of its diversity. Vegetarian, vegan, kosher, etc., there were always lots of options.

Social and Town Life:

1.) Describe the school's town and surrounding area.
Cheshire is a small idyllic town in Connecticut. It's close to New Haven and a short drive or train to NYC or Boston, but the town itself is very small and does not offer much as far as entertainment or shopping (within walking distance).
2.) Describe the social life at your school - what did you like most about it?
There was always so much to do and participate in. Again, I liked the international aspect of the school.
Read more details about Cheshire Academy on their 2023 profile page.

Alumni Reviews Review School

Cheshire Academy Alumni #1
Class of 2017
5.00 8/5/2019
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. . .
Cheshire Academy Alumni #2
Class of 2016
5.00 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. . .
Cheshire Academy Alumni #3
Class of 2005
5.00 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. . .
Show more reviews (2 reviews)

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Quick Stats (2023)

  • Enrollment: 343 students
  • Yearly Tuition (Boarding Students): $57,250
  • Yearly Tuition (Day Students): $29,850
  • Acceptance rate: 45%
  • Average class size: 10 students
  • Application Deadline: Feb. 1 / rolling
  • Source: Verified school update