Resources and updates for the 2023-2024 school year are available here

Dear Alumni,

As an alumna, I am one of many who consider Cheshire Academy a home away from home. A place that births vision, opportunity, and a community where you learn to become a globally educated citizen.

One of my primary goals as the Director of Alumni and Family Relations is to solidify long-lasting relationships and connectivity between CA and the alumni community. I encourage you to consider what kind of impact you may want to have through fellowship with one another during volunteering opportunities, and alumni events. I’d also like to invite you to stay in touch and network by joining one of our regional alumni chapter Facebook groups. Whether you are from the Class of 1967 or 2020, Cheshire Academy has something for you; our common experiences and aspirations are what hold us together and make us stronger. It is my honor to partner with extraordinary individuals as we build, grow, and invest in the future of Cheshire Academy.

Continue to visit our website to learn about the exciting and new opportunities CA will be hosting and, if you should find yourself in the area, stop by Bowden Hall to connect with the Advancement team! We’d be happy to answer any questions you have or update you on the latest events around campus.

With warmest regards,
Kayla Burroughs Lipsitz ’10
Director of Alumni and Family Relations

Upcoming Alumni Events


Friday, May 31 – Saturday, June 1

Held at Cheshire Academy, this special annual event will take place conveniently while our students celebrate prom! 

CAPFA will be auctioning off a number of fun, unique, and priceless items and experiences to bid on to raise money for our organization.

Homecoming Weekend

Friday, October 18 - Saturday, October 19

SAVE THE DATE! We’re already planning to welcome you back for Alumni Homecoming Weekend. The football game begins Saturday at 4 p.m. and we hope to see lots of you in the stands!  

Will CA Be In Your Area?

Stay in the Know

Make sure your contact info is up to date so you don’t miss us and your fellow alumni when we’re passing through! Fill out our contact form today.

Stay in Touch

Class Notes: What's New With You?


Please let us know what and how you are doing—work, family, milestones, achievements, travels, recognitions, or any other notes you want to share with the community. You can read class notes in print and online on Issuu. Fill out the form below and upload your related photos.

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Regional Alumni Chapters
Remain connected with fellow CA Cats near you.

Cheshire Academy has launched regional chapters in cities all over the globe, providing alumni with a meaningful way to stay connected with each other and the Academy. Led by local volunteers with support from the Alumni Leadership Association (ALA) and the school’s Office of Advancement, CA alumni have opportunities to come together like never before.

Regional chapters aim to sponsor anywhere from two to six social and networking events per year, including—but not limited to—happy hours, gallery exhibitions, guest speakers, and other cultural programs. This new platform is a great way to locate and network with fellow CA Cats living or working in your area.

For more information on a regional chapter near you, to join a regional chapter Facebook Group or if you are interested in starting a new regional chapter in your city, please contact Kayla Lipsitz ’10, Director of Alumni and Family Relations.

Cheshire Academy regional alumni chapters include:

Fairfield and Westchester Counties
New York City
Washington D.C.


Cheshire Academy has partnered with Parchment to order and send your transcript and other credentials securely. This link will open a new browser.


Cheshire Academy is excited to offer a new, merit-based Legacy Scholarship in the amount of $10,000 for children, grandchildren, and relatives of Cheshire Academy alumni.

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