Grayson came to Mount Holyoke in 1977. He was a professor of religion and philosophy, and also served as Interim Dean of the Chapel in 1997-98. He was popular as a teacher, several times being elected as the Baccalaureate speaker. He specialized in 19th century American and German philosophy of religion. He sought to create an atmosphere of “debate, discomfort, and adventure.” Grayson was also a lecturer for the United States Information Service in Western Europe and Africa and was a senior Fulbright research fellow in Tübingen Germany studying German philosophy.
In 1985 he traveled to South Africa at the invitation of local groups to deliver lectures on aspects of American culture. Before leaving, he laid down three conditions to the South African government – he would not carry a passport stamped “honorary White”, he would meet with Black South African leaders, and he would be permitted to lecture at Black universities and integrated audiences everywhere. While on his trip he met with Winnie Mandela who had been honored at the Mount Holyoke commencement in 1985 and granted an honorary degree although she was unable to travel to accept it. He also met with Desmond Tutu and members of the African National Congress. Grayson retired in 2013.