Gilkes taught at a number of universities in the Caribbean, Canada and the United Kingdom over the past 40 years, including at the University of Kent at Canterbury, the University of Warwick, the University of Guyana, the University of the West Indies (where he served as Reader in English and Head of the English department) in Barbados and the Sir Arthur Lewis Community College in St. Lucia. He was a Quillian Visiting Professor at Randolph-Macon Woman's College. In Bermuda he directed plays and taught a theatre workshop put on by the Department of Community & Cultural Affairs at The Berkeley Institute.