This study explores the art of interpretation in works of history, art, music, and literature from the medieval period. The authors demonstrate that the search for meaning was a primary concern of medieval authors and that the history of medieval thought from Augustine to Aquinas and Ockham illustrates the dialectic of question and answer that is the foundation of hermeneutics. This study is the first to offer a diversity of hermeneutic approaches and themes in the context of medieval works. The study’s interdisciplinary approach to the medieval works considered invites analysis from scholars and critics in all areas of medieval studies. The breadth of scope in addressing the art of interpretation in the various disciplines also provides a valuable general introduction to medieval culture.