Independent School Magazine Features Cheshire Academy Head Tom Woelper
Woelper discusses his path to Cheshire Academy and what inspires him in the Fall 2026 issue of Independent School Magazine Recently, Cheshire Academy Head of School Tom Woelper appeared on the National Association of Independent Schools (NAIS) podcast Member Voices to trace his career, how the school is addressing the widespread challenges of financial stability and AI in the space, and the enduring need for empathy and […]
Cheshire Academy Convocation: New Students, New Mascot Name, New Year
New traditions, speeches, songs, and a name for the Cheshire Academy Cat mark annual ceremony on Simosa Field Cheshire Academy opened its 2026-27 academic year on Monday, September 7, with a lively Convocation, featuring songs and speeches from students, and the unveiling of the school mascot’s forever name. A large crowd of family, friends, and alumni attended the event under picture-perfect skies. The 233-year-old school, […]
10 New Faculty Join Cheshire Academy for 2026-27
Each brings a wealth of experience and talent to academics and student support services Cheshire Academy welcomed 10 new faculty members for the 2026-27 academic year, including classroom teachers and student-facing professionals in College Counseling, Campus Life, and the Roxbury Center for Learning & Leadership. “Cheshire Academy continues to attract talented and experienced faculty and staff and I’m looking forward to working with each of […]
Hearst Media Spotlights Cheshire Academy’s Approach to Language Learning
Connecticut’s largest media chain explores how language develops the brain and global citizenship Cheshire Academy’s comprehensive approach to language learning took center stage in a Hearst CT Media Group feature story that ran in the Connecticut Post, Greenwich Time, Stamford Advocate, and several other state newspapers. At CA, students from around the globe are discovering that learning a language is about far more than words—it’s about becoming a different kind of thinker, and a different kind of citizen. […]
‘They Believed in Me Before I Did:’ Cheshire Academy’s Class of 2026 Marks a Milestone Commencement
An alum returns as keynote speaker, a new tradition takes root, and 111 graduates carry CA’s lessons forward Cheshire Academy held its historic 232nd annual Commencement Exercises June 6 in a festive celebration of chances taken and given and the school’s faith in each student’s burgeoning potential. Under sunny skies and a warm wind, the […]
Cheshire Academy Head of School Featured on National Independent School Podcast
Connecticut Boarding School Leader Joins NAIS “Member Voices” to Discuss Navigating a 230-Year-Old Institution Through Uncertainty Cheshire Academy Head of School Tom Woelper P’26 was invited to share his leadership philosophy on Member Voices, the official podcast of the National Association of Independent Schools (NAIS), in an episode released June 1, 2026. The 43-minute conversation […]
UVA Associate Professor, Alum is 232nd Commencement Speaker
Christi Lockwood ’04 Will Address Building a Life of Chances Taken Christi Lockwood ’04, Ph.D., associate professor of management at University of Virginia, will be the keynote speaker for the 232nd Cheshire Academy Commencement Exercises on Saturday, June 6. The 9 a.m. ceremony will take place on Kevin Slaughter Memorial Field, with 111 seniors and postgraduates expected to receive their diplomas. “Cheshire’s willingness to give me a chance as a […]
Cheshire Academy to Welcome Award-Winning Author Jason Reynolds for All School Read
MacArthur Fellow to visit campus Sept. 29 to discuss his acclaimed Long Way Down Jason Reynolds, who has won the Newbery Medal, NAACP Image Award, and 2024 MacArthur “Genius” Fellowship, is the keynote speaker for Cheshire Academy’s annual All School Read program on Tuesday, Sept. 29. As required summer reading for all Cheshire Academy students, the entire community will read his acclaimed book Long Way Down as a stepping-off point for a series […]
Honduras Trip is Unforgettable Experience for One Cheshire Academy Junior
Madelyn Ventola ’27 hopes to return to the orphanage where she volunteered Madelyn “Maddy” Ventola ’27 has a spring recess she’ll never forget. While she and her family have traveled to the Bahamas, St. Kitts, and St. Lucia on previous school breaks, this year she and her mom flew to El Progreso, Honduras, where they spent […]
Cheshire Academy Seniors “Celebrate the Yes” to College Decisions
Personalized College Counseling Guides Students to ‘Right-Fit’ Decisions to Impressive List of Top Schools Cheshire Academy celebrated its seniors and postgraduates on Friday, May 1, with the annual Celebrate the Yes party, followed by a fun day of outdoor games, a special lunch, and the annual Faculty/Students Basketball Game, organized by the Student Council. The day was […]
