Glass attended the Bread Loaf Writers' Conference in 1978, where he studied with Howard Nemerov. In 1979, Glass attended the Johns Hopkins University Writing Seminars and obtained his M.A. in English. His teachers there were Richard Howard and Cynthia Macdonald. Fellow students included Michael A. Martone, Lucie Brock-Broido, and Louise Erdrich. In 1980, Glass moved to Milwaukee, Wisconsin, to attend graduate school at the University of Wisconsin–Milwaukee. While in Milwaukee, he edited the "Cream City Review", and was constantly in touch with the readings and artistic events at Woodland Pattern Book Center. During this time, Glass began to correspond with Helen Adam, Kathleen Raine, Armand Schwerner, Rosmarie Waldrop, Ronald Johnson, Larry Eigner, Ron Silliman, Ian Hamilton Finlay, Steve McCaffrey, Robert Peters, Bern Porter, Lewis Turco, and others involved in new and experimental literature. Glass graduated with a Ph.D. in English, with an emphasis in American literature, in 1988.