Sherwood was raised in New Jersey on the east coast of the USA. His early years included a B.S. in Zoology from Washington State University, construction work in Antarctica, Peace Corps in Tanzania, Academic Director for the School for International Training program in Kenya, and experience in student affairs administration at Washington State University, Cornell University, and finally at Penn State University as the Assistant Director for Residence Life. After, he received his doctorate from Ball State University. Sherwood then came to the University of Vermont in 1995 on a doctoral fellowship. At UVM he has served as the Assistant Director for the ALANA Student Center, Director of the Race & Culture Program, and currently has appointments as Lecturer in the College of Education and Social Services and Director of the Center for Cultural Pluralism. During the summer, he was a member of the faculty for the Summer Institute for Intercultural Communication (SIIC) in Portland, Oregon where he has taught for many years. His work involves faculty and staff professional development trainings on issues of culture and social justice, conducting research, and teaching graduate and undergraduate courses in Educational Foundations and Human Development.