Alumni Relations and Events


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

Virtual Alumni Event
Thursday, Jan. 25, 6:30 p.m.

Please join Head of School, Julie Anderson P ’19 ’23, and fellow alumni/ae for a casual conversation about all things reunion happening this spring from May 31 to June 1st. If your class year ends in 4 or 9 we hope to see you! We also welcome all alumni to attend the event.

Register Today


Reunion 2024
Friday, May 31 – Saturday, June 1 Details TBA 

Class Notes

Share 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. 

Class Notes
Click or drag a file to this area to upload.

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
Baltimore and Washington D.C.

Transcript Request

Order Transcripts

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

Legacy Scholarship

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.

Learn more: Legacy Scholarship

Alumni Contact Information


We want to be in touch. Please complete the form below so that we can update your records. Your contact information allows us to notify you regarding alumni events, benefits and exciting developments at Cheshire Academy.