Richard “Dick” Whitcomb, 1955

Educational Leader and Philanthropist
Dick Whitcomb grew up feeling he really had no option for going to college. He was the youngest of three children raised by a single mother in the working-class village of Bellows Falls, Vermont. “I was brought up by my grandfather,” Dick explains, “And that was kind of tough for me.” With determination and the support of others, Dick went to college, became an educational leader and philanthropist, and changed countless lives with his significant achievements.  

Athletics gave Dick opportunity. He was a star for Bellows Falls’ football, basketball, baseball, and track teams, which were renowned in Vermont. He was an all-state football player in his junior and senior years and was the leading basketball scorer in southern Vermont. Vermont Academy gave Dick a full scholarship for a post graduate year. He became a more confident student while adding to his athletic accomplishments, becoming the leading scorer in basketball and track as well as in the New England Prep School semifinals played in the original Boston Garden.  

“I loved my experience at Vermont Academy! It gave me the opportunity to pursue a college education on a full athletic scholarship and ultimately two master’s degrees, all fully paid – finally ending up as headmaster at St. Luke’s School for 24 years. Who would have guessed! If I have attained any success along the way, I can attribute a good deal of it to Vermont Academy.”

Dick wanted to be a teacher, a coach, and ultimately an athletic director. These are all milestones he achieved early in his career at St. Luke’s School in New Canaan, Connecticut. In his twenty-four years as headmaster, Dick became a legend on the St. Luke’s hilltop. He built a community known for its warmth and devotion to every student. Enrollment increased from 190 students to 300 students in just three years. The school’s endowment drastically increased, and he helped grow the Richard M. Whitcomb St. Luke’s Scholarship Endowment Foundation, devoted to students in need, to $6.5 million. Dick was the first headmaster in the three-state Fairchester Athletic Association to be recognized by the Urban League for his work with minority students.

Dick’s early years as a coach helped him to build a natural and authentic style of communication so that everyone brightens up when they see him. People around New Canaan call him “Coach,” and they share what is in their hearts and minds, showing their deep respect for this man who inspired athletes and made St. Luke’s a leader in character education, academics and athletics. His community work in Connecticut is renowned, as he has supported countless organizations including Norwalk’s Carver Center, the New Canaan Community Foundation, Norwalk Community College, New Beginnings Family Academy, and more. Dick possesses a special gene for making everyone around him feel hopeful, important, recognized, and part of his “team.”  That team is focused on transforming the lives of young people and hardworking, dedicated adults, opening horizons of possibility for them.

Dick’s roots in Vermont run deep and his philanthropic work shows how much the area means to him. When the University of Bridgeport named him a Distinguished Alumni in 2019, he quipped, “I got to go back to Bellows Falls and tell the people I’m distinguished, because I guarantee they won’t believe it.” The Richard and Barbara Whitcomb Foundation has given tens of thousands of dollars to Bellows Falls area organizations over the years, including the Bellows Falls Area Senior Center, Parks Place Community Resource Center, Our Place Drop In Center, and the Greater Falls Warming Shelter. Vermont Academy has benefited from Dick’s generosity as well. 

Dick’s background and the people he grew up with in Bellows Falls have led him to focus his life on helping people. As for his own success, Dick says, “I’ve never been big on individual accomplishments. I don’t think anyone can be successful individually. You can’t accomplish anything without the support of others.”

In helping so many others follow their dreams, Dick has become a distinguished educator and community supporter. 

We are proud to award Dick Whitcomb the Florence R. Sabin Class of 1889 Distinguished Alumni Award.
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Vermont Academy is a coed college preparatory boarding and day school in southern Vermont, serving grades 9-12 plus a postgraduate year.