Son of the Yale University professor of history Leonard Woods Labaree and Elizabeth Mary Calkins, Benjamin Woods Labaree was raised in New Haven, Connecticut, and attended The Hotchkiss School.
[3] In 1958, he received an appointment at Harvard University, rising from instructor to assistant professor of history and Allston Burr Senior Tutor.
In 1963, he was appointed dean of Williams College, in Williamstown, Massachusetts, serving in that role until 1967.
Between 1977-1989, he was director of the Williams College-Mystic Seaport Program (commonly called Williams-Mystic) at Mystic Seaport Museum, Mystic, Connecticut, 1977–89; director, Center for Environmental Studies at Williams College, 1989–92; and professor of history and environmental studies, 1989–92.
[2] Closely associated with Professor Robert G. Albion of Harvard University, Labaree succeeded him as Director of the Frank C. Munson Institute of American Maritime History in 1974.