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 […]
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 […]
Record Number of Prospective Families Welcomed at Open Houses
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
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 […]
