Cheshire Academy Announces 2025 Town Scholar 

CA “party bus” delivers with a four-year scholarship for Ava Dasilva  Cheshire resident Ava Dasilva probably wondered why her parents had such a long list of chores for her to do around the house on March 6. She got her answer at 10 a.m. when Director of Admission Rebecca Brooks drove the Cheshire Academy “party […]

1794 Challenge Surpasses Goals, Raising More than $200,000

More donors than ever support key Cheshire Academy Annual Fund initiatives  A record 383 donors took part in the 1794 Challenge: Cheshire Gives, raising more than $203,000 to help keep Cheshire Academy one of the best independent schools in the country.  The 1794-minute campaign – s-purred on by creative “Catflix” videos that parodied popular TV […]

Lift Every Voice 

Cheshire Academy pauses to celebrate, reflect during Diversity, Equity, Inclusion & Justice Community Weekend  Chill winds did nothing to lessen the warmth of Cheshire Academy’s annual Diversity, Equity, Inclusion & Justice Community Weekend, a celebration of the values that make the international school a welcoming place for all.   “It was heartwarming to see our […]

Hustle & Heart – Cheshire Academy Lacrosse

Cheshire Lacrosse has a storied history and high hopes for the future  If you were going to start a private school lacrosse program in 1962, you’d be hard pressed to find a better coach than Cheshire Academy’s choice for their fledgling team: Stewart Lindsay.  A three-time All-American selection at Syracuse University in the 1950s, he […]

Cheshire Academy Expands Mental Health Offering  

Partnership with Uwill offers teletherapy and crisis support for students at the Academy    NATICK, MA— February 6, 2024 — Cheshire Academy, today, announced a partnership with Uwill, the leading mental health and wellness solution for students, to enhance the existing counseling capabilities with expanded counseling and a crisis connection. Uwill’s proprietary technology facilitates immediate […]

Cheshire’s Reynolds ’24 Shines for Penn State Football 

Freshman Tight End Plays in College Semifinals, Makes Key Surprise Play  Cheshire Academy football standout Luke Reynolds ’24 is already making a name for himself as a first-year tight end for the Penn State Nittany Lions, even catching a pass in this month’s semifinal nailbiter against Notre Dame.   Dubbed “a centerpiece of Penn State’s […]

10 Things to Know About Cheshire Academy’s New Head of School Tom Woelper

Tom Woelper

On January 1, longtime educator Tom Woelper will take the reins as Cheshire Academy’s next head of school. You may know that he was the founding head at New England Innovation Academy in Massachusetts, that he’s worked at Groton, Taft, and Hotchkiss or that he was head of school at the American Pacific International School in […]

TEAM PLAYER: Riley Norwood ’20

A Commencement honor fuels a life of character and commitment to others Each year at Commencement, Cheshire Academy bestows the Jennifer Hawke-Petit Recognition Award on a deserving senior who emulates the late nurse’s wisdom, expertise, caring, and kindness. The 2020 recipient, Riley Norwood ’20, was no exception. “Riley accepted that award and made it her […]