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Record Number of Prospective Families Welcomed at Open Houses

Cheshire Academy Open House

Third visit day planned to highlight signature academics, support, and more  More than 250 people attended two Fall Open Houses at Cheshire Academy in October and November, respectively – getting an insider’s view of the unique blend of challenging courses, varied athletics and activities, and peerless college counseling and support this close-knit community offers.  Interest was […]

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 […]

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 […]

Remembering Former Cheshire Academy Head of School Jerry Larson

JERRY LARSON

Beloved former head passed away August 27 after a battle with cancer  It is with great sadness that we share that former Cheshire Academy Head of School Dr. Jerry Larson, of Bristol, RI, has passed away after battling cancer. Larson was Head of School from 1999-2004 and returned as Interim Head for two more years from […]

Cheshire Alum wins DOC NYC 40 Under 40 Recognition 

Scott Ruderman'09 receives award at Cheshire Academy

Cheshire Academy Hall of Famer best known for award-winning documentary Scott A. Ruderman ’09, a 2024 Cheshire Academy Hall of Fame inductee, was named to the 2024 DOC NYC 40 Under 40 list spotlighting young creatives making an impact on the field of documentary through their powerful work and diverse voices.   Ruderman was recognized for […]

CA alum Alexis Holmes ’18 wins gold at Paris Olympics 

Track star anchors women’s 4x400m relay, runs personal best in solo 400m sprint Class of 2018 track star Alexis Holmes won a gold medal at the 2024 Paris Olympics this month, anchoring the winning team in the women’s 4x400m relay just a day after running a personal best time in the women’s 400m.  Cheshire Academy’s […]

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