Dobelle holds bachelor's, master's, and doctoral degrees in Education Administration from the University of Massachusetts Amherst, and a master's degree in public administration from Harvard University. Elected mayor of Pittsfield, Massachusetts in 1973 and 1975, Dobelle was later Massachusetts State Commissioner of Environmental Management and Natural Resources. He was U.S. Chief of Protocol for the White House in the Carter administration with the rank of Ambassador. His wife Kit served as Chief of Protocol and Chief of Staff to First Lady Rosalynn Carter.