Winglass was born in Cambridge, Massachusetts and graduated from Springfield College in 1957 with a B.S. in education. He also earned a M.A. in international affairs from George Washington University in 1969. While in the Marine Corps, Winglass was decorated with a Navy Distinguished Service Medal and three Legion of Merit awards. He lived in Bath while serving as Labor Commissioner and, shortly before resigning, sold his Bath home and moved to his retirement home in Surry. He is married to Norma Winglass and they have four children.
