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 […]
Football Showcases Bring 100+ College Coaches to Campus
Annual Recruiting Days highlight opportunities for student-athletes More than 100 coaches and recruiters from top-tier colleges and universities converged this spring on Simosa Field to scout our student-athletes, one of the many opportunities Cheshire Academy creates for those hoping to play in the future. The sessions also provide students a chance to discover the many […]
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 […]
From Cheshire to Forever: A Love Story
A Twin’s Hunch Leads Two Cheshire Academy Alums to a Campus Proposal Salena Khan ’20 didn’t think twice when English teacher Nicole Beaudwin P’26 asked if she could come to campus for a “Where are They Now?” interview for the Cheshire Academy yearbook. After all, she had worked on The Rolling Stone when she was a student, and she looked forward to spending some […]
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 […]
Cheshire Academy Teacher Tapped as International Speaker for Middle States Association AI Demo Day
Stephen Murray Discussed AI-Assisted Feedback on Student Lab Reports Cheshire Academy Science Teacher Stephen Murray was one of four teachers from around the world invited to share how they leverage generative AI in the classroom for the Middle States Association’s first-ever AI Demo Day. Based in Philadelphia, the MSA is a worldwide leader in accreditation and school […]
College Fair Draws 135+ International Colleges & Post-Grad Programs
Cheshire Academy Hosts One of Largest College Fairs in Connecticut Cheshire Academy students had an exclusive chance to engage with representatives from 135 colleges and universities at the 23rd annual College Fair on Wednesday, April 15. In addition, representatives from ROTC, summer programs, and the Connecticut Higher Education Supplemental Loan Authority (CHESLA) were on hand to help students and […]
MIT Technology Review Makes Cheshire Academy a Case Study in AI Adoption
CA Experts Explain Teaching Responsible Usage, Model Best Practices Two Cheshire Academy faculty members provided their expertise for MIT Technology Review’s special newsletter on AI in education. The Education edition of “Making AI Work” provides practical guidance for working professionals about how generative AI is being deployed, including detailed commentary from Librarian and Technology Coordinator George Aiello and Miriam […]
