The Foundation for a Meaningful Life
Kindergarten - Grade 9 in Southborough, MA

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Documenting the Spirit of Fay: Meet Dick Gilcreast

by Erin Ash Sullivan
Readers of this magazine over the years may recall seeing gorgeous black-and-white photos of Fay from the mid-to-late 1900s— images of boys (and later, girls) in classrooms, on the playing fields, and in the dorms. Nearly all of these images were captured by Dick Gilcreast, a photographer whose ties to Fay run deep.
Readers of Fay Magazine over the years may recall seeing gorgeous black-and-white photos of Fay from the mid-to-late 1900s— images of boys (and later, girls) in classrooms, on the playing fields, and in the dorms. Nearly all of these images were captured by Dick Gilcreast, a photographer whose ties to Fay run deep.

The son of legendary English teacher Seaver Gilcreast and brother-in-law of beloved faculty member Dick Upjohn, Dick Gilcreast’s connection to Fay began in 1953 when his father began teaching at Fay. Newly graduated from Williams College, Dick actively pursued photography until he was drafted in 1955; after a stint in the Navy that included two years of photographing the Blue Angels down in Pensacola, Dick found himself back up in New England. He joined Fay’s faculty in 1959 and for the next twelve years taught a range of courses that included English, history, and some of Fay’s very first science classes. (It’s true: Fay did not teach science until the 1960s!) In 1972, Dick left Fay to pursue a successful freelance career, and his photos appeared in publications including U.S. News and World Report and Yankee Magazine.

Over the next four decades, Dick returned to Fay frequently to document campus life. His photo shoots for Fay continued through 2009—a staggering 56 years of storytelling through images. 

Our archives here at Fay are full of Dick’s photographs. His images captured Fay at a time that in some ways feels long gone— but the energy, thoughtfulness, and humor that infuse his photos of students across the decades speaks to a spirit and joy that is common to all Fay students regardless of the era.

This fall, Dick returned to campus with a few more boxes of photos that he uncovered at his house. We are delighted to share some of them with you here—and we look forward to showcasing more of them in the updated pictorial
History of Fay School, which covers the years 1866 to 2018 and is due out this spring.

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