Cheshire Academy - Review #3

Read more details about Cheshire Academy on their 2024 profile page.
Cheshire Academy

About the Author:

Years Attended Boarding School:
Sports and Activities:
I was a 4-sport varsity athlete (soccer, cross country, swimming, and track), sang in our school's a cappella group, was in two school musicals, and served on various committees. I was class secretary, vice president of our school's community service club (the Ich Dien society), and was a head tour guide.
College Enrolled:
Syracuse University
Home Town, State:
Beverly, MA

Reflections and Advice:

1.) What do you think makes your school unique relative to other boarding schools?
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 that was offered, which my father found would be perfect for my less-than-academically-inclined brother. And it was. He loved the program and the school, and he enrolled in the fall and was a student in the Roxbury tutoring center. Roxbury is one of the most notable parts of Cheshire, and I'm not sure that other schools have anything like it. It's a tutoring center, but the tutors who work there are full-time, and there are a variety of options for students who choose (or are required) to use its services. It's also open to students who aren't enrolled in the Roxbury program, and acts as another option for help outside the classroom. I also really appreciated that us boarding students had mandatory study hall between Sunday and Thursday nights, from 8-10 pm. It conditioned me incredibly well for my arrival at college.
2.) What was the best thing that happened to you in boarding school?
Now that I'm about to graduate from college and start grad school, my main focus are my academics. Back when I was in boarding school, because of the structure of it all, I was really appreciative of all the different aspects of my life. Had I gone to a public school, I'm not sure I would have been able to be involved in so many different sports. I'm not sure I would have had all the same opportunities, as there would have been hundreds of students in line ahead of me. Cheshire gives its students vast opportunities. It really helped me mature, too. Boarding school does force students to grow up quickly, but it also means that by the time you get to college, you're already ahead of everyone else.
3.) What might you have done differently during your boarding school experience?
I felt a bit lucky when I started at Cheshire since my older brother was already there, so I had a group of older students that I knew, and I was already very familiar with the campus. Despite that, I was homesick for the first couple weeks, but never after that. I wish I had tried a couple different sports. Lacrosse always looked fun to me, but I was very wedded to running. I would tell incoming students to value the experience. Having dorm parents is one of the coolest things, especially when they're in their mid-20s; they are relatable and eager to help students. I had wonderful relationships with my dorm parents, who were also my coaches and teachers. I even ran a half-marathon with two of them my senior year!
4.) What did you like most about your school?
I liked how it felt like home. I had great relationships with the faculty and staff, especially my dorm parents, and they are still role models for me today. I like that there are opportunities for everything, and that if there aren't, the school is open to trying to facilitate them for students. I loved the diversity, and I love that it's even more diverse now. I remember my junior year going to dinner at the headmaster's house - I imagine that at a larger school, students might not even meet the headmaster. I can't pick one thing I liked the most - it really all culminated into a great experience for me.
5.) Do you have any final words of wisdom for visiting or incoming students to your school?
Mr. B's pizza down the street from campus has the best slice in town, and Cheshire Coffee's peanut butter mocha frappe is unbeatable. I lived in the three girl's dorms on campus - Motter, Horton and Hurley, and loved them all. Motter is the most modern, but Horton and Hurley have a certain charm to them. Cheshire was an incredible experience for me, and I wouldn't have done high school any differently. I love the school, and I hope that other students have the same great experiences I did while I was there. It will always feel like home.


1.) Describe the academics at your school - what did you like most about it?
I was in the 'guinea pig' year of the International Baccalaureate program, for which I was a full diploma student. While I didn't end up getting the diploma, I did take classes I may not have otherwise, which I think is one of the strengths of the program. I took a history class with a teacher who had served as my older brother's academic advisor, and thus with whom I was familiar. He went on to be a great mentor for me, and I'm grateful to this day that I was lucky enough to take his class. The academic options at the school are abundant. I was studying at a French level above what the school offered, yet I was still accommodated. Had that not been the case, I may not have gone on to study French in college and spend a semester abroad in France.


1.) Describe the athletics at your school - what did you like most about it?
I was a competitive athlete, though I was never the best. As competitive sports were required for two out of the three seasons of the year, everyone really had to participate, but it didn't feel forced. At CA, there was always a place for athletes like me. The fact that there were 4 or 5 boy's basketball teams when I was a student is evidence of this. Every student, regardless of their athletic ability, was encouraged to participate. Our football, men's basketball, and volleyball teams were championship teams when I was a student, and they continue to be. Sports were a source of pride for us.

Art, Music, and Theatre:

1.) Describe the arts program at your school - what did you like most about it?
I was quite involved in the arts while I was at Cheshire! I sang in our school's a cappella group, CATS (Cheshire Academy Through Sound) and participated in two musicals. In addition, because I did the IB program, I was also required to take two years of studio art. Not being very visually inclined in the arts, it was a class that I struggled with at first, but with the guidance of one of the school's greatest teachers, Francois Poisson, I came to truly enjoy it. The best part of his class was that you were able to succeed even if you couldn't draw, or paint, or sculpt; many of our assignments were art critiques, which I found I was quite good at.

Extracurricular Opportunities:

1.) Describe the extracurriculars offered at your school - what did you like most about it?
One of the extracurricular activities that I was most involved in was being a tour guide. I knew I loved the school from the beginning, and I wanted a way to share that with others. I was very committed to it, and my junior year I was selected, with 6 other students, to be head tour guides. We got to help select new tour guides, train them, and play more of a role in the admissions process, which was rewarding - we'd put in a lot of work, and we got to see it pay off. I was also involved in the community service club, and during my senior year, earned an award for my involvement. I also remember a couple students reviving our school newspaper my junior or senior year, which was incredible. They took it into their own hands, since they thought it was an important thing for the school to have, and it turned out incredibly successfully.

Dorm Life:

1.) Describe the dorm life in your school - what did you like most about it?
Living in a dorm can be incredibly difficult, but it also has the possibility of being very rewarding. You're given a sort of extended family, and it can be great always having that resource. I liked living in single rooms better than having a roommate, so I did that for my last two years. I loved my dorm parents the most, especially when they would bake for us. I think back then I wished the rules were more lenient about girls and boys being able to visit each other's dorms, but now I can appreciate more why that wasn't allowed.


1.) Describe the dining arrangements at your school.
The dining set up is a bit different now than when I was a student. I understand there are now more family-style, sit-down dinners where students sit in assigned groups with faculty and staff. This was only down for Thanksgiving when I was there, and I'm glad to see they've expanded it. Thursday night was ice cream night, which we all loved. The food options were good, with a wide variety of healthy choices. I ate quite well when I was there.

Social and Town Life:

1.) Describe the school's town and surrounding area.
Cheshire is a quaint little Connecticut town. It's home to the best coffee shop I've ever been to, Cheshire Coffee, where every academy student spent their Sundays. I miss their drinks even today, 4 years after I graduated. As a long distance runner, the bike path in town was great for me, and we used it frequently during cross country and track seasons. There's a grocery store within walking distance, as well as several restaurants and pharmacies. I think it's a pretty ideal setting for a school. It's a small town, but it's not so rural that students feel trapped on campus.
2.) Describe the social life at your school - what did you like most about it?
I loved that everyone was on the same schedule! Classes ended at 3:30 and sports practices would start at 4 or so and go until 5:30 or 6. Then it was dinner and free time until 7:50, when we had check-in in our dorms for study hall. Being social is incredibly easy when everyone is working on the same schedule, and I think I took that for granted a bit when I got to college. Additionally, the fact that students are required to do sports means that everyone ends up interacting with a lot of people they may not have otherwise. The school is a bit larger now than when I was there, but I imagine it's still the same sort of deal where everyone knows everyone. It's very close-knit.
Read more details about Cheshire Academy on their 2024 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 1980
5.00 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. . .
Cheshire Academy Alumni #3
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. . .
Show more reviews (2 reviews)

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Quick Stats (2024)

  • 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