Leadership Overview

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. Here 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 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.

The 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

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. 


Cheshire Academy
10 Main Street
Cheshire, Connecticut 06410

MAIN PHONE: 203-272-5396
MAIN FAX: 203-250-7209
ADMISSION OFFICE: 203-439-7250
ADMISSION FAX: 203-439-7601
ATHLETICS OFFICE: 203-439-7242 

About Cheshire Academy

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  • The Student-Centered Private School in Connecticut.

    We put the unique needs of every student first. That’s why we offer a flexible program that allows students to mix academic course tracks with athletics and/or fine arts programs, according to their needs and interests. Students can stretch their intellectual boundaries by taking one of 20 advanced International Baccalaureate® Diploma Programme courses, or practice new skills by participating in a range of afternoon programs including; athletics, fine arts, and performing arts. We are also the only Connecticut private school to offer one-on-one student coaching through our Roxbury Academic Support Program.
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