Cheshire Academy to Welcome Award-Winning Author Jason Reynolds for All School Read

Jason Reynolds

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

Cheshire Academy College Decision Day

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 […]

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 […]

MIT Technology Review Makes Cheshire Academy a Case Study in AI Adoption

MIT Technology Review Cheshire Academy

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 […]

Coed Fencing Medals at 2026 State Championships

Cheshire Academy Fencing

Men’s Épée Take Bronze, Four Fencers Rank The Men’s Épée team of Cheshire Academy Coed Fencing earned bronze at the Connecticut State High School Fencing Team Championships over spring break, with four CA fencers ranking the top 30 at Burton E. Moore Connecticut High School State Championships.  Eve Raymond ’27, of Cheshire, CT, placed 10th in Women’s Saber and […]

Varsity Boys’ Basketball Reaches NEPSAC Championship Game

Cheshire Academy Basketball 2026

Cats Log Thrilling Post-Season Run to Kick Off Spring Recess On Sunday, March 8, 2026, the Cheshire Academy Varsity Boys’ Basketball Team took the court in a championship game against top-seeded Cushing Academy. They came up short on the scoreboard—Cushing won 64-55 – but the Cats played with tenacity and teamwork. “I have watched a lot […]

Lindsay Shaw ’01 Tumbles into a Life of Sports and Scholarship

There are moments in the lives of many high school students when a mentor offers something that ends up changing the course of their young life. Such was the case for Lindsay Shaw ’01 when Head of School Dr. Jerry Larson gave her a book on sport psychology. Lindsay isn’t sure, but she thinks it […]

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