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 […]
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 […]
Should Teachers Still Give (and Grade) Homework?

An English teacher at a private high school breaks down the neuroscience-backed truth about what actually benefits student-learning and brain development. Trained in Mind Brain Education (MBE) research, Cheshire Academy teachers are lifelong learners and experts in their fields. We asked them to share their thoughts and scholarship on vital issues in education. Cheshire Academy English Department […]