Pickering graduated from the BVI High School (today called the Elmore Stout High School) in 1976. He went on to study at the University of the West Indies, Cave Hill Campus, Barbados. He later earned Bachelor of Medicine and Bachelor of Surgery degrees from the University of the West Indies, Mona Campus, Kingston, Jamaica. He later also earned a Doctor of Medicine degree from the University Hospital of the West Indies, Mona Campus. He is a fellow of the American College of Obstetrics and Gynecology, Washington, D.C.
