The Inside Story

What does it feel like to be a part of the community at Cheshire Academy? The best way to find out is to come to campus and talk to our students.

The second best way is to take a look at this website. We asked a diverse group of students—we won’t say typical Cheshire Academy students, because there is no such thing— to share ideas and feelings about their lives here at the Academy. 

From day students from Connecticut to international students from Germany, from varsity athletes to theater buffs, we asked our students to share their stories. Enjoy the videos, explore the related programs, and get to know us! 

Hannah '14

To the Boston Conservatory and Beyond
Hannah, an international student from Germany, debunks misconceptions about American students and describes how the world school atmosphere at Cheshire Academy sets the stage for new friendships.
Read More.

Day Student | International | Theater

Gabe '14

Gearing Up for College
Gabe discusses why he entered the PG Program at Cheshire Academy. His goals range from bringing up his grades to attending a better college, and he explains how the college counseling program at the Academy helped him achieve his dream.
Read More.

PG Student | Day Student | College Counseling

Jacky '16

Living on Campus
Jacky '16 knows what it's like to live with a best friend. He tells the Inside Story about his experience living with a roommate from Germany and describes his favorite community weekend. 
Read More.

Boarding Student | International Student

Christian '04

Giving Back
Christian '04 is a former Cheshire Academy tennis star and Venture Grant recipient. He now works in the Alumni Relations and Development Office here at the Academy.
Read More.

Alumni | Venture Grant | Tennis

Giselle '15

Diving Into Theory
Giselle, a boarding student at Cheshire Academy, has always loved math and science. She shares how the IB Program has allowed her to delve into these subjects in new and interesting ways. 
Read More.

IB Program | Varsity Athlete | Boarding Student

Mrs. Monahan

Dorm Life
From living in the dorm with her husband, Mr. Monahan, to teaching history in a 1:1 iPad program, Mrs. Monahan shares what life is like as a teacher and dorm parent at Cheshire Academy.
Read More.

Faculty | Dorm Parent | History Teacher

Grace '17

Day Student on Campus
Grace '17 has tried a little bit of everything. From dance to Mandarin-- and even photography-- she's taking advantage of all the Cheshire Academy community has to offer.
Read More. 

Day Student | Dance Program | Mandarin Program

Jacob '16

Flipping the Classroom
Jacob '16 is a Roxbury student and a technology whiz. He shares his experience in the Roxbury Program, as an IB student, and as a participant in the very exciting ropes course afternoon activity! 
Read More.

Roxbury Student | Day Student | IB Program


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSIONS FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 

About Cheshire Academy

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  • The student-centered private school in CT

    Cheshire Academy is a boarding school in Connecticut that challenges students in grades 9-12 and Post Grad 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. 
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