Welcome Alumni

Cheshire Academy has more than 6,000 alumni around the world. They are invited back to campus throughout the year for longstanding traditions like Homecoming Weekend and Reunion, along with many other special regional events. Cheshire Academy also offers networking opportunities, family events and panel discussions.  


We encourage our alumni to stay connected. Alumni are a part of Cheshire Academy’s rich history and also vital to its bright future. Share your news with us, volunteer or drop by for a Red Door photo at Bowden Hall!


Reunion Weekend – June 10-12, 2022


Cheshire Academy is excited to welcome all alumni back to campus. Click here to learn more.


Legacy Scholarship


Cheshire Academy is excited to offer a new, merit-based Legacy Scholarship in the amount of $15,000 for children, grandchildren, and relatives of Cheshire Academy alumni.

Learn more: Legacy Scholarship


1794 Magazine


Cheshire Academy’s award-winning magazine 1794 is published twice a year and is mailed to alumni, parents, and friends of CA. Check out the latest issue and back issues from previous years.


Red Door Photos


Stop by campus and take part in Cheshire Academy’s Red Door photo tradition! Check out our Red Door gallery on Flickr.



225th Anniversary Alumni Directory


The Office of Advancement is excited to publish the new directory that comes on the heels of the Academy’s historic 225th anniversary. 

Learn more: 225th Anniversary Alumni Directory


If you missed the application deadline…


The Admission Office continues to accept applications for the 2022-23 school year.


Apply Today


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