WTNH News 8 Spotlights Cheshire Academy Linebacker Vince Reno ’27

Star Senior Talked About College Prospects, Growing Up in a Football Family Vince Reno ’27, the youngest of a family of football standouts, talked about his prospects for college play and what it’s like to be the son of former Yale University head coach Tony Reno and brother of Yale’s current quarterback, Dante, in an interview with WTNH News 8. “I grew up with it,” […]
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 […]
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 […]