Kate Heartfield’s 2018 interactive novel invites a contemporary audience to join Chaucer and his fellow pilgrims on their way to Canterbury. This text-based game—or game-like text—enables the reader to make choices about the direction of the narrative in the fashion of earlier hypertext literature and the old Choose Your Own Adventure novels for young readers and other so-called ‘gamebooks.’ Based primarily on my experiences teaching The Road to Canterbury in an upper-level English course at a large public university, this essay reflects on how one might teach Heartfield’sinteractive fiction alongside Chaucer in mutually illuminating ways and in a variety of course settings.