A diverse group of pilgrims traveling to the shrine of Thomas Becket in Canterbury engage in a storytelling contest to pass the time. The pilgrims, representing various social strata of 14th-century England, aim to win a free supper by telling the most entertaining and instructive tales. They face the physical constraints of the road and the social tensions inherent in their disparate backgrounds, which often manifest in the content of their stories. The narrative framework utilizes a frame story structure, where the host of the Tabard Inn acts as the moderator for the unfolding competition.

Readers and critics frequently analyze the work for its complex portrayal of medieval social hierarchies and human behavior. Discussion often centers on the interplay between the pilgrims' personalities and the specific tales they choose to recount during the journey. Scholars highlight the text as a primary example of late medieval literary innovation, noting the balance between bawdy humor and serious moral inquiry. Many readers appreciate the accessibility provided by modern verse translations, which allow for a clearer understanding of the wit and irony embedded in the original text.