David Dickinson attended Tufts University, the Museum of Fine Arts School, and the Paier School of Art. He developed the visual art curriculum at Stoneleigh Burnham School before taking a position in Deerfield’s Fine Arts Department in 1987. Holder of the John S. Hilson Chair in the Fine Arts, he has created a drawing/painting curriculum that includes sequential courses from the introductory level to post-AP tutorials. Galleries in the United States and Canada have represented David’s paintings and illustrations, and the New York Art Directors’ Club and the Art Directors’ Club of Boston have honored his published work. In 1985, David was one of forty art instructors recognized nationally by RISD for teaching excellence. He also earned the "Lifetime of Influence" honor from the NFAA in 2008. He and his wife Claudia, a member of the Academy's Foreign Language Department, live in Academy Lane House.
David has also coached girls varsity tennis since 1992.