Cheshire Academy’s Roxbury Center Named to Top 15 NAIS Global Innovations
The National Association of Independent Schools report includes programs in Luxembourg, the U.A.E., Canada, Mexico, and the U.K. Cheshire Academy’s forward-thinking Roxbury Center for Learning & Leadership is one of the top 15 international success stories in the National Association of Independent Schools (NAIS) “2026-27 NAIS Education Innovations Around the World.” Roxbury joins eight programs from across the United States, one of only […]
Cheshire Academy Head Talks Personalized Learning, AI on National Podcast
Woelper weighs in on “How Adaptive Learning Changes Teaching Without Replacing It” Cheshire Academy Head of School Tom Woelper discussed how students can develop independent thinking skills with the help of AI, while still maintaining the crucial connection, guidance, and encouragement from teachers on the national podcast “The Brighter Side of Education.” Woelper discussed the evolving role of teaching in an AI world with Dr. Lisa […]
Cheshire Academy Announces New Parent Education and College Finance Series
New workshops, Zooms, and school resources give parents the tools they need and strengthen school-home connections Cheshire Academy is excited to announce two new series of workshops on parenting issues and financial literacy, providing parents and families with up-to-date information to make smart, informed decisions for their students. “A strong partnership between home and school is key to […]
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 […]
