Remembering Cheshire Academy Trustee Emeritus David Jepson ’59

Beloved alum, former trustee, passed away Oct. 8, 2025

It is with heavy hearts that we share the passing of former trustee and true son of Cheshire Academy, David Jepson ’59.

David was a graduate of Cheshire in 1959 receiving the Costin Cup, the award for the student who most improved while at the school. David always said that was the best part of his CA experience, forming him into the student that went on to be a great success in life.

While we often see a person recognized as a longtime friend and supporter, David was truly a friend to Cheshire Academy since the early ’80s. During the Bicentennial in 1994 he volunteered to be the Class Agent for his class and actively reached out to classmates for the 200th anniversary. From there his involvement grew, eventually becoming a Trustee in the early 2000s and serving as a Trustee again in 2015-2018. In 2019, David was awarded Trustee Emeritus status. 

David had an outgoing and friendly personality and was able to be a friend and mentor with many alumni from many different generations. In 2019, he was the second recipient of the D. Robert Gardiner Arts and Letters Hall of Fame award for his work in architecture, an award of which he was very proud.

David loved the arts and sat on the boards of the Wadsworth Atheneum and New Britain Museum of American Art. He also served as a tri-chair for our Cheshire Academy Community Arts and Athletics committee.

He will truly be missed by all who knew him.

To view an obituary for David, please visit Legacy.com.

Aerial view of the town of Cheshire, CT
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