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 […]
How Cheshire Academy Developed a New Signature Program for a Global Education
Global Citizenship Distinction brings school’s mission to life through individualized pathway By Marc Aronson, Dean of Academics, Cheshire Academy When I joined the faculty of Cheshire Academy in the fall of 2008, it’s fair to say the school was at something of a crossroads with its academic program. Like many New England independent schools at […]
Cheshire Academy Student, Wallingford Resident, to Compete at World Championships of Irish Dance
Grayson Solan ’27 taps into love of dance and family heritage Hours of dedicated practice and precision skill – as well as a bit of Irish luck – will send Grayson Solan ’27 to both the World Championships of Irish dance, Oireachtas Rince na Cruinne, in Dublin in April and the North American Championships in Washington, DC, […]
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 […]
GRADUATING CLASS: Three retiring teachers reflect on their time and legacy at Cheshire Academy
The 102nd episode of “The Twilight Zone.” “The Changing of the Guard,” focuses on Professor Ellis Fowler, a gentle teacher facing retirement after 51 years at a boys’ prep school in Vermont. Thumbing through the pages of old yearbooks, he’s convinced his lessons have been disregarded, that he has given his students “nothing, nothing at […]
10 Things to Know About Cheshire Academy’s New Head of School 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 […]
Scary Good: Kyle Alex Brett ’05
A thrilling ride from a corporate lawyer to a creative executive for the team behind the hit chiller “Speak No Evil” Kyle Alex Brett ’05 instantly related to director Jordan Peele’s Oscar-winning film “Get Out.” First, the film reminded him of a short story he wrote in college. Second, he was a corporate lawyer for […]
Record Number of Prospective Families Welcomed at Open Houses
Third visit day planned to highlight signature academics, support, and more More than 250 people attended two Fall Open Houses at Cheshire Academy in October and November, respectively – getting an insider’s view of the unique blend of challenging courses, varied athletics and activities, and peerless college counseling and support this close-knit community offers. Interest was […]
Niche Gives Cheshire Academy an A+ in 2025 Rankings
The Academy receives high marks for diversity, activities, college prep in national survey Cheshire Academy received an overall grade of A+ in the 2025 Niche ratings of high schools across the nation. The independent boarding and day school ranked in the top 150 of boarding schools in the United States and was in the top […]
