10 Things to Know About Cheshire Academy’s New Head of School Tom Woelper
On January 1, longtime educator Tom Woelper will take the reins as Cheshire Academy’s next head of school. You may know that he was the founding head at New England Innovation Academy in Massachusetts, that he’s worked at Groton, Taft, and Hotchkiss or that he was head of school at the American Pacific International School in […]
TEAM PLAYER: Riley Norwood ’20
A Commencement honor fuels a life of character and commitment to others Each year at Commencement, Cheshire Academy bestows the Jennifer Hawke-Petit Recognition Award on a deserving senior who emulates the late nurse’s wisdom, expertise, caring, and kindness. The 2020 recipient, Riley Norwood ’20, was no exception. “Riley accepted that award and made it her […]
Cheshire Academy Announces Global Citizenship Diploma Distinction, Honors Designations
Major academic overhaul provides more unique pathways to college, opportunities to achieve Cheshire Academy today announced an exciting new Global Citizenship Diploma Distinction, a leadership pathway recognizing top-caliber work, as well as other curricular enhancements to make already cutting-edge course offerings even more dynamic, relevant, and forward-thinking. The changes will provide rigorous, personalized learning opportunities, […]
Scary Good: Kyle Alex Brett ’05
A thrilling ride from a corporate lawyer to a creative executive for the team behind the hit chiller “Speak No Evil” Kyle Alex Brett ’05 instantly related to director Jordan Peele’s Oscar-winning film “Get Out.” First, the film reminded him of a short story he wrote in college. Second, he was a corporate lawyer for […]
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 […]
