fbpx

SCHEDULE A VISIT TODAY! CLICK HERE

Cheshire Academy written in white lettering with a solid dark blue background.

A Studio of One’s Own: Cheshire’s Art & Music Majors Prepare Future Artists

The Art and Music Majors offer promising artists space to experiment, learn, and prepare for a creative life A pristine gallery to display paintings, sculptures, and imaginative installations. Ample opportunities to play and sing for a live audience. Dedicated studio and practice space. These are just a few of the benefits Cheshire Academy’s Art and […]

Unlocking Potential: 25 Years of Roxbury Academic Support

Becca Yimlamai ’25 has a lot on her plate. Part of both the Asian Student Union and the Jewish Student Union, she is a member of Eco Leaders and a student leader of The Coleman Group, a campus mentorship club that aims to empower young women. She was elected as treasurer of the National Honor […]

Niche Gives Cheshire Academy an A+ in 2025 Rankings 

The Academy receives high marks for diversity, activities, college prep in national survey  Cheshire Academy received an overall grade of A+ in the 2025 Niche ratings of high schools across the nation. The independent boarding and day school ranked in the top 150 of boarding schools in the United States and was in the top […]

Two Former Classmates Return from the World Stage for Alexis Holmes Day 

Class of 2018 alums Alexis Holmes (Team USA Olympian) and Tara Lynch (award-winning journalist) joined the CA community to celebrate the Olympic gold medalist  Cheshire Academy on Friday, Nov. 8, celebrated Alexis Holmes Day, with a lively student body Q&A and a football halftime celebration with the 2024 Olympic gold medalist, a Class of 2018 alum.  […]

Mariotti, Triplett Join Cheshire Academy Board of Trustees

The two new members bring a wealth of knowledge from the enrollment and legal fields, respectively. Two new members of the Cheshire Academy Board of Trustees – Martha S.Triplett and Kristen A. Mariotti – bring professional experience and enthusiasm for independent, global education to their new posts. Elected at the board’s May meeting, they may […]

7 Factors to Look for in a Private School Academic Support Program 

A customized approach to prep school academics can turn struggle into success  When it comes to helping students reach their potential during the secondary education years, one size does not fit all. Many students benefit from the guidance of a trusted, skilled instructor to help them recognize their strengths and secure the tools and strategies […]

Inaugural Health & Wellness Weekend Helps Students Energize and Relax 

Chill Out! Cheshire Academy takes time for student wellness on new Community Weekend  The entire Cheshire Academy family learned ways to promote self-care and build community during Health and Wellness Weekend. One of five Community Weekends planned throughout the academic year, the three days of programming offered students, faculty, and staff time to unplug and […]

Join Us for Alexis Holmes Day: Friday, Nov. 8 

Cheshire Academy to celebrate Olympic champion and alum at football game vs. Suffield Academy  Please join Cheshire Academy in welcoming back 2018 alum and 2024 Olympic gold medalist Alexis Holmes on Friday, November 8. Holmes will be here at her alma mater speaking with students in a Q&A session led by fellow alum and four-time […]

Woelper named next Cheshire Academy Head of School

Nationwide search results in appointment of experienced private school leader  The Cheshire Academy Board of Trustees on Oct. 17 announced the appointment of J. Thomas “Tom” Woelper as the next head of school of Cheshire Academy upon the recommendation of the Search Committee and the unanimous approval of the Board. The announcement was made after […]

Cheshire Academy Trustee Petit wins Human Spirit Award 

Dr. Petit honored for forming foundation to address education, illness, and violence issues  Dr. William A. Petit, Jr., a member of the Cheshire Academy Board of Trustees, is one of five inaugural winners of the Denise D’Ascenzo Foundation Human Spirit Awards. Dr. Petit will be recognized Saturday, Nov. 9, at the 2024 Human Spirit Awards Dinner, which […]

Privacy Policy

Third Party Pixels and Cookies

When you visit our website, log in, register or open an email, cookies, ad beacons, and similar technologies may be used by our online data partners or vendors to associate these activities with information they or others have about you, including your email address. We (or service providers on our behalf) may then send communications and marketing to these email addresses. You may opt out of receiving this advertising by visiting https://app.retention.com/optout.