Clubs and Activities

There is always something to do at Cheshire Academy! The number of clubs, activities, student publications and performance groups is extensive and often grows or changes to meet the interests of the students. There truly is something for everyone.

Afternoon Activities

The Afternoon Program is a part of our philosophy at Cheshire Academy, and is as important and inclusive as the academic, social, and residential facets of each day. We strongly believe The Afternoon Program helps each student to acclimate and take pride in contributing to something bigger than themselves. By incorporating the Eight Pillars of Bowden into our daily language both on and off the fields, it’s our mission to teach life lessons through each afternoon program we offer our students.

Below you will find a list of all non-competitive afternoon activities offered in The Afternoon Program, followed by a link to our competitive athletic offerings, which must comprise two out of three seasons for each student. Some afternoon programs qualify as competitive athletic offerings; please inquire with the Dean of Students and Athletics.

If you have any questions about the below afternoon activities, please contact the athletic office at 203-439-7242.

The Varsity Players

The Varsity Players is Cheshire Academy’s student theater troupe. Three times a year, the Varsity Players put on a fantastic show that gets students involved in all aspects of the theatrical world, ranging from acting, singing and dancing to set design, lighting and costumes. Students may choreograph the musical, select musical accompaniments, and even secure the student musical troupe to fill the pit, depending on their interests. The Varsity Players is open to committed actors as well as to burgeoning artists. It is one of several components that make up Cheshire Academy’s outstanding theater program, and students interested in pursuing theater as a career option are encouraged to enroll in the IB Theater course, as well.

Community Service

Cheshire Academy values giving back to the community, which is why we allow students to substitute one competitive athletics offering for a season of immersive community service. From recycling to our annual blood drive, participants in the community service afternoon activity know that they’re making a difference. In addition, students are welcome to suggest community service projects for the community service afternoon activity, Since this activity is part of The Afternoon Program, the proposed community service project must be substantial and require a minimum of four hours a week.


The annually published Rolling Stone, Cheshire Academy’s yearbook, is a herculean project produced by a committed team of students and their faculty coaches. In honor of the amount of effort and teamwork needed to produce a quality document of 100+ pages, participants in the yearbook may substitute one competitive athletic offering to join the club. Student participants may photograph campus events, format yearbook pages, and write copy for selected images. In addition, students are responsible for choosing pictures for the yearbook and organizing content for pages, which may include working with seniors, parents, and community partners.

Leadership Activities

Leadership opportunities at Cheshire Academy can be found in the academic program, as well as outside the classroom. Every day, teachers, coaches, advisors, dorm parents and even department heads call on students to be leaders of group activities, projects and events. In these roles, students take on significant responsibilities and their actions greatly contribute to the strong sense of community at the Academy.

The main student governing body is the Student Leadership Council that is comprised of class presidents, a postgraduate representative, and leaders of the National Honor Society, Ich Dien Society, Captains Council and International Students Association. They meet regularly with the Associate Dean of Students to give advice and support to administrators, faculty, staff and students. Other leadership opportunities include prefects, class officers, peer counselors, Ich Dien Society, athletic team captains and more.

Certain leadership opportunities hold a formal application process, such as Prefects, Peer Counselors and the Citizenship Committee, which are chosen by faculty. Other leadership opportunities, like the Ich Dien Society, hold student elections for key leadership positions. Below are some of the ways you can get involved as an Academy Student Leader.

Admission Ambassadors

At boarding schools like Cheshire Academy, the Admission Ambassadors serve a huge role in the life of the school. Admission Ambassadors meet prospective families, give campus tours, participate in panel discussions, and work with various departments on campus for special projects. However, their main responsibility is to share the Cheshire Academy experience with prospective students and families. Their time and effort give prospective families a taste of the authentic Cheshire Academy experience and is vital to the life of the Academy.

Athletic Team Captains

Each team typically designates two or three individuals on the teams as captains. Captains typically have demonstrated strong leadership, knowledge and skill within the sport, ability to work with team members and serve as a motivator within the team. Assuming the this leadership position means acting as a role model for teammates, assisting coaches with practices, encouraging teammates and more.

Captains Council

Made up of all varsity captains, this group meets with the athletic director and the deans to discuss issues that go on with the teams and how they can be more helpful in leadership situations on campus. The captains are charged with promoting team and school spirit opportunities and working together to present the final memories of the season at the three sports banquets. Captains are essentially extensions of the athletic department and coaching staffs, and are expected to be leaders in our community, both on and off the fields and courts.

Ich Dien Society

The Ich Dien Society is a student-run community service organization. As a group, the students run two annual blood drives, a Pennies for Patients drive to fight childhood leukemia, and a school-wide Breast Cancer Awareness campaign during parents weekend to support the Play for the Cure National Foundation for Cancer Research. This gives students a way to help their local community as well as the greater global community in which they live.

The International Student Association (ISA)

The International Student Association (ISA) is an organization committed to providing a caring and supportive environment for Cheshire Academy students from around the world. Students plan activities, create conversations, celebrate the global Academy community, and reach out to the Cheshire town community through service learning.

Peer Counselors

Cheshire Academy’s peer counselors are a select group of students who understand the culture of the Academy and have been trained to help new students adjust to boarding school. Working with the Academy’s director of counseling, these students each work closely with both new students, and anyone in need of help. They are expected to be role models within the community.

National Honor Society

National Honor Society (NHS) is more than just an honor roll. The NHS chapter establishes rules for membership that are based upon a student’s outstanding performance in the areas of scholarship, service, leadership, and character. These four criteria for selection form the foundation upon which the organization and its activities are built.

Scholarship: students who have a cumulative grade point average of 3.33 or higher (with an Honors, IB or AP course) or 3.66 or higher (without an Honors, IB or AP course ) meet the scholarship requirement for membership. “These students are then eligible for consideration on the basis of service, leadership, and character.”(NHS Constitution, Article IX, section 2)

Service: This quality is defined through the voluntary contributions made by a student to the school or community, done without compensation and with a positive, courteous, and enthusiastic spirit.

Leadership: Student leaders are those who are resourceful, good problem solvers, promoters of school activities, idea-contributors, dependable, and persons who exemplify positive attitudes about life. Leadership experiences can be drawn from school or community activity while interacting with or for others.

Character: The student of good character upholds principles of morality and ethics, is cooperative, demonstrates high standards of honesty and reliability, shows courtesy, concern and respect for others and generally maintains a good and clean lifestyle. The Cheshire Academy chapter also uses the Pillars of Bowden as standards of good character.


One of the highest offices of student leaders at the Academy, Prefects play an important role in the residential program. A position for juniors or seniors, Prefects work to uphold community standards in the dorm, positively add to the boarding school program and model good citizenship.

Citizenship Committee

Members of the Citizenship Committee are elected to their positions for their history of upstanding citizenship at Cheshire Academy. These students sit on disciplinary committee meetings and help determine consequences for violations of Cheshire Academy’s disciplinary code.


Black Student Union

Members of BSU will educate all people about the importance and influence of black culture around the United States. We serve as a place where black students can bond through our shared culture while having meaningful conversations centering around issues related to race, social justice and inclusion.


CA LEAPS The Cheshire Academy Leadership Experience and Advancement Program for Students (CA LEAPS) is an action-oriented group of students who are invested in developing the skills they need to be the leaders of tomorrow.  The Leadership Club will sponsor on-campus speakers, will take on leadership roles within the community by planning and executing different events, and will contribute to conversations about community culture and climate-focused around the 8 Pillars of Bowden. Members of the club will also have the opportunity to attend off-campus leadership conferences and workshops, and network with student leaders from other schools throughout New England.

Candy Club

The Candy Club explores the diverse world of candy with weekly offerings and discussions centering on candy from the USA and around the world. 

Chess Club

In this club, participants will have the opportunity to learn chess and improve their playing skills. Chess is a fun game that incorporates many aspects of the active learner profile: knowledgeable, inquirers, thinkers, communicators, principled, open-minded, caring, risk-takers, balanced, and reflective. The Chess Club will foster your intellectual growth in a fun and relaxed atmosphere, and improve your critical-thinking skills.

The Coleman Group

The Coleman Group is an action-oriented association of dynamic women who create a positive environment of experience and learning, enrich the lives of young women, and provide support to advance the mission of Cheshire Academy. Each year, the Coleman Group sponsors two major symposiums, hosts six informal “Girl Talk” meetings, and a senior recognition reception and pinning ceremony.

The Den (Spirit Squad)

The Spirit Squad is focused on offering opportunities for school spirit and involvement.  Participants will attend athletic events, theater and musical performances, sponsor fundraisers, support weekend activities and more. Our mission is to represent the academy with a spirit of support for our teams, fans and the entire CA Community.  Spirit is the feeling or pride and loyalty that exists among the members of a group and community that helps to make the members of the group do their best.

Discussion Club

Like art? Musical theater? Music videos? The Discussion Club is made up of a group of friendly intellectuals who take turns selecting a short piece of art that they believe will stimulate conversation. After that, we talk about it. Discussion is unstructured and the goal is for everyone to have plenty of time to just talk. The club was initially intended for students who might speak less in class or who are looking to gain confidence with a spoken English vocabulary—but it’s a welcoming space for anyone who’s looking for intelligent and thought-provoking conversation.

Diversity Club

Diversity Club embraces different cultures and strives to create a world with better understanding and open-mindedness. We build connections with each other and whomever to initiate well informed and meaningful conversations. We welcome all and encourage everyone to join.


The Eco-Leaders is a student leadership organization committed to advancing environmental sustainability at all levels; individual, community and nationally. Eco-leaders approach sustainability from both an environmental as well as economic and cultural perspective. Students lead campus and community projects such as Beach Clean-ups, Earth Day celebrations, dorm recycling and much more.

Gay/Straight Alliance

The Gay/Straight Alliance is a group of students who are allies for those who not only identify as Gay or Transgender, but who identify as a minority. The GSA sponsors social and educational events that celebrate diversity and individual differences. The group is a member of True Colors and GLAAD: statewide organizations that provide resources and support to GSAs.

Global Student Union

The Global Student Union (GSU) is a group of students who work with the International Student Coordinator to organize trips and activities that highlight our diverse Global community. Two unique events are our One World Different Cultures Day in the fall and our International Festival Weekend in the winter. During OWDCD we invite Juniors and Seniors to work with faculty members to put together an educational presentation that highlights their culture or heritage. They spend an afternoon presenting to our school community. During our International Festival Weekend, students, their families and our faculty and staff come together to represent their respective cultures and celebrate their traditions. This exciting annual event is full of traditional food, music, and performances.

Ich Dien Society

The Ich Dien society is a student-run community service organization.  Projects have included: two annual blood drives, a Pennies for Patients drive to fight childhood leukemia, and a school-wide Breast Cancer Awareness campaign during parent’s weekend to support the Play for the Cure National Foundation for Cancer Research. This gives students a way to help their local community as well as the greater global community in which they live.

Le French Club

Like trying different foods? Want to learn how to prepare mousse au chocolat or soupe à l’oignon? How about French music like Stromae and Angèle? And French manners –how do I cut the cheese or which fork do I use? Let’s (virtually) visit Versailles, Notre Dame Cathedral, Mont St. Michel and Quebec City! Love French movies like les Choristes and Intouchables?  How about cartoons like Tintin, Asterix and the Minions? What is the origin of cul-de-sac, May Day!, déjà-vu and RSVP? Want to learn about the art of Matisse and Monet? Where are Nice, Nancy, Condom and Brest???  Ever heard of Christian Dior, Coco Chanel, Louis Vuitton?  So much to see and so much to do: what do YOU want to learn about French culture.

Math Club

The CA Math Club meets weekly to practice a range of questions in preparation for high-level math contests, designed to challenge even the most gifted high school mathematician. Representatives from the Math Club participate each year in regional, national, and internationally recognized contests and competitions, including the American Math Competition (AMC), The Math League, the Harvard-MIT Math Tournament, and the Math Majors of America Tournament for High Schools (MMATHS) at Yale.

Model United Nations

Model United Nations is an academic simulation of the United Nations through which delegates debate, collaborate and attempt to solve wide-ranging international issues of immense importance. In so doing, participants develop skills in diplomacy, cooperation, and critical thinking that motivate lifelong global citizenship. Cheshire Academy’s Model United Nations group travels to Yale’s MUN conference each January.

The Paw Print

“The Paw Print,” is the Cheshire Academy student-run newspaper written by the students, for the students. Writers have the choice of writing about a wide variety of topics such as politics, world news, sports, upcoming holidays, and more.

Student Ambassadors

Want to give campus tours to prospective students & their families?
Want to be a part of a student’s decision to come to CA?
Want to show pride in your school? #GO CATS!
Want to make a difference?
Become an Ambassador!

Strategy Board Game Club

This club plays strategy board games, primarily Axis & Allies and it variants, but is open to playing other strategy games.

The Tea and Go Club

The Tea and Go Club is dedicated to drinking tea and playing go. We will drink tea from China, Japan, India, and Vietnam. The Go Club is open to anyone from novice to master. We have members who can teach you the game and members of the CA Community who play at very high levels.