Category: Alumni

Best-selling Author Mark Kurlansky ’66 Visits Classes, Gives Public Book Talk 

Award winner toured campus, met with students hoping to follow in his footsteps  Mark Kurlansky ’66, an award-winning author of more than 40 books, stopped by Cheshire Academy February 19, visiting several classes and signing books before an evening author talk at Barnes & Noble Cheshire.  Kurlansky met with aspiring writers in the Writing Center and addressed classes in both history […]

Remembering Cheshire Academy Alum James Van Der Beek ’95

Class of 1995, Cheshire Town Scholar, 1977-2026 It is with profound sadness that Cheshire Academy mourns the passing of James Van Der Beek ’95, who died on February 11, 2026, following a courageous battle with colorectal cancer. He was 48 years old. James embodied everything the Cheshire Town Scholar award represents: scholarship, citizenship, ambition, and […]

Cheshire Academy Alum Molly Golden to Headed to Super Bowl LX 

Sophomore is youngest Ithaca College student ever to cover the Big Game from the official Super Bowl Media Center and Radio Row  Molly Golden ’24 is headed to California to report on Super Bowl LX for Ithaca College, where she is a sophomore. Golden, who started the popular “Molly’s Minute” Instagram series while at Cheshire Academy, is the youngest-ever student to be […]

Cheshire Academy Reignites Community Tradition with Lights of Hope Event

Community invited to experience luminaries, support local charities on December 17  CHESHIRE, CT – Cheshire Academy is bringing back a cherished community tradition this December with the return of Lights of Hope, an evening event that celebrates service, unity, and the power of giving back.  A Beloved Tradition Returns  Inspired by the original Lights of Hope […]

Chicago Bears VP, Cheshire Academy Alum Returns to Inspire Football Team 

Pat McCaskey ’68, corporate secretary and vice president of the Chicago Bears, came back to Cheshire Academy for Homecoming Weekend 2025, enjoying dinner with the football team and offering inspiring words before their victorious match-up against Brunswick School.  “He had dinner with us in Bowden Hall, which is big for the kids because they see […]

Never Give Up, Never Grow Up: Alum’s Journey from Cheshire Cat to Furby

Richard C. Levy ’64  Many students come to Cheshire because of its academic reputation, top-notch college counseling, or chance to catch the eye of NCAA Division I university coaches.   For Richard C. Levy ’64, it was all about the jacket.  While touring Cheshire Academy, he took one look at the school’s navy wool classic emblazoned […]

Caring Alum Makes a Difference at Ann Hewan Foundation

Exposure to international issues at Cheshire opened a whole new world for one caring alum  Others might look at the forlorn field behind Goodwill School in Montego Bay, Jamaica, and see uneven ground, rubble, and the odd tree stump.  Jaida Williams ’19 sees opportunity.  By creating a soccer field behind the school Williams’ parents attended, […]

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 […]

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 […]

Class of ’63 Alum’s Love for Lacrosse Never Flagged 

Alumnus Spotlight: Mickey-Miles Felton ’63 Mickey-Miles Felton ’63 started playing lacrosse at Cheshire Academy in 1963 and his love for the game has led to a lifetime of involvement, including plans to volunteer at the 2025 JCC Maccabi Games® near his Tucson home this summer.  The games, which will take place from July 27 through […]