Medievalism has experienced an enormous popularity in the last decades, if not century, but the specific contributions by the Baltic German author Werner Bergengruen have not yet received full attention. In light of a selection of his novellas, we can identify him as a meaningful respondent to medieval themes, ideas, concepts, and values which he dealt with rather creatively, employing them for his own ethical, religious, or spiritual musings. Studying Bergengruen’s novellas makes it possible not only to familiarize ourselves once again with one of the most popular German authors from the mid-twentieth century who has unfairly lost in popular appeal maybe since ca. 1970. Through his novellas we also gain intriguing keys to open innovative perspectives toward a variety of literary and didactic texts from the Middle Ages, which are not simply imitated here, but emerge as critical catalysts or sources for Bergengruen’s own reflections on timeless human issues.