How Language Drives Purpose: Refreshing Cheshire Academy’s Mission 

In the age of AI, you’d think refreshing an independent school’s mission statement would be as easy as typing a few key words into a text box and hitting “Go!”  But, at Cheshire Academy, our mission – both the goals and aspirations behind it and the words that form it – is carefully considered. So, […]

11 New Faculty and Staff Members Join the CA Team 

Each brings a wealth of experience and talent to the community Cheshire Academy welcomed 11 new faculty and staff members for the 2025-26 academic year, including two CA alums. The cohort includes new faces in the classrooms, as well as the Roxbury Academic Support program, athletic training, and the health and counseling departments.  “We are […]

AJ Soldra ’23 drafted by the L.A. Dodgers 

Soldra is the first Cheshire Academy alum to be drafted to Major League Baseball. AJ Soldra ’23, a former post-graduate outfielder at Cheshire Academy, was chosen by the Los Angeles Dodgers in the 16th round of the 2025 Major League Baseball draft.  Cats Head Baseball Coach Anthony Giano  P’19,’20,’23 certainly isn’t surprised.  “He had tremendous […]

How to use AI in the Classroom: A Guide

Student smiling over latop looking at another student Cheshire Academy

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. George Aiello is academic technology coordinator and librarian at Cheshire Academy, having held similar positions in schools in Hong Kong, Paraguay, and Singapore. Before making the career change to education, […]

Former Cheshire Academy QB Reno Talks to NY Times on Yale Move 

Quarterback Dante Reno ’24, who led the Cheshire Cats to a league championship in 2023, was interviewed by the New York Times about his decision to play football at Yale University, where his dad, Tony Reno, is head coach.   The announcement made sports news across the country, with stories about the novel father-son arrangement in […]

Cheshire Academy Presents Diplomas to 97 Class of 2025 Graduates

Deserving students, faculty hero honored at historic Academy’s 231st Commencement – plus, three sets of twins graduate in the Class of 2025! Cheshire Academy held its 231st annual commencement exercises May 31 in a festive celebration of individual journeys and the promise the future holds for its new graduates. Despite cool breezes and intermittent rain, […]

Cheshire Academy Teacher Advances to Van Cliburn Piano Finals

Cheshire Academy piano teacher Vitaly Starikov is one of six finalists in the Van Cliburn International Piano Competition, considered one of the most prestigious music competitions in the world.   The competition was founded in 1962 to celebrate Cliburn’s victory at the 1958 Tchaikovsky Competition in Moscow. Twenty-eight of the world’s best young pianists traveled […]

Guiding Photography Students from Looking to Seeing 

The journey of visual thinking beyond passive observation into active perception  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.   Antonio Alfaiate is the photography and digital imaging educator at Cheshire Academy. His diverse teaching background includes college art […]

Cheshire Academy Quarterback Featured on ESPN Podcast

Cheshire Academy Quarterback Keegan Croucher ’27 got some airtime on the popular national podcast ESPN College GameDay, after he garnered interest at the May 12 Football Showcase.  During the segment “On Pete’s Radar,” hosts Rece Davis and Pete Thamel discussed Croucher as a top 2027 prospect who was one of several CA standouts who drew […]

Postseason Brings Victory in Three Sports at Cheshire Academy

Cheshire Academy Girls' Varsity Lacrosse Championship

Girls’ Lacrosse scores first-ever WNEGL championship, while softball wins back-to-back titles, and three track athletes medal Cheshire Academy athletes celebrated across the state last weekend as Varsity Girls’ Lacrosse clinched their first-ever WNEGL title, three track athletes won medals at the New England Preparatory School Athletic Council (NEPSAC) Division II Championships, and Varsity Softball won its […]

VIRTUAL OPEN HOUSE

June 16, 2026, 6-8 p.m.

Discover everything we have to offer, meet faculty, and ask questions live, all from the comfort of your home.