In April, with the beginning of spring, people of varying social classes come from all over England to gather at the Tabard Inn in preparation for a pilgrimage to Canterbury to receive the blessings of St. Thomas à Becket, the English martyr. Chaucer himself is one of the pilgrims. That evening, the Host of the Tabard Inn suggests that each member of the group tell tales on the way to and from Canterbury in order to make the time pass more pleasantly. The person who tells the best story will be awarded an elegant dinner at the end of the trip. The Host decides to accompany the party on its pilgrimage and appoints himself as the judge of the best tale.
Shortly after their departure the day, the pilgrims draw straws. The Knight, who draws the shortest straw, agrees to tell the first story — a noble story about knights and honor and love. When the Knight finishes his story, the Host calls upon the Monk. The drunken Miller, however, insists that it is his turn, and he proceeds to tell a story about a stupid carpenter. At the end of his story, everyone roars with laughter — except the Reeve, who had once been a carpenter. To get back at the Miller, the Reeve tells a lowbrow story about a cheating miller. At the end of The Reeve's Tale, the Cook, Roger, promises to tell a true story, but he doesn't complete his tale.
By now, the first day is rapidly passing, and the Host hurries the pilgrims to get on with their tales. Using the best legalese that he knows, he calls upon the Man of Law for the next tale. The Man of Law proceeds to tell the tale of Constancy. The Host is very pleased with the tale and asks the Parson to relate another one just as good. The Parson declines, however, and rebukes the Host for swearing and ridiculing him (the Parson). The Shipman breaks in and tells a lively story to make up for so much moralizing.
The Wife of Bath is the next to tell a story, and she begins by claiming that happy marriages occur only when a wife has sovereignty over her husband. When the Wife of Bath finishes her story, the Friar offers his own tale about a summoner. The Host, however, always the peacekeeper, admonishes the Friar to let the Summoner alone. The Summoner interrupts and says the Friar can do as he likes and will be repaid with a tale about a friar. Nevertheless, the Friar's tale about a summoner makes the Summoner so angry that he tells an obscene story about the fate of all friars and then continues with an obscene tale about one friar in particular.
After the Friar and Summoner finish their insulting stories about each other, the Host turns to the Clerk and asks for a lively tale. The Clerk tells a story about Griselda and her patience — a story that depicts the exact opposite of The Wife of Bath's Tale. The Merchant comments that he has no wife as patient and sweet as Griselda and tells of tale of a young wife who cheats on her old husband. After the Merchant's tale, the Host requests another tale about love and turns to the Squire, who begins a tale of supernatural events. He does not finish, however, because the Franklin interrupts him to compliment the Squire on his eloquence and gentility. The Host, interested only get in getting the next story told, commands the Franklin to begin his tale, which he does. The Franklin tells of a happy marriage.
Then the Physician offers his tale of the tragic woe of a father and daughter — a story that upsets the Host so much that he requests a merry tale from the Pardoner. The Pardoner tells a tale in which he proves that, even though he is not a moral man, he can tell a moral tale. At the end of the tale, the Pardoner invites the pilgrims to buy relics and pardons from him and suggests that the Host should begin because he is the most sinful. This comment infuriates the Host; the Knight intercedes between the Host and the Pardoner and restores peace.
The pilgrims then hear a story by the Prioress about a young martyr. After the seriousness of this tale, the Host turns to Chaucer and asks him for something to liven up the group. Chaucer begins a story about Sir Topas but is soon interrupted by the Host, who exclaims that he is tired of the jingling rhymes and wants Chaucer to tell a little something in prose. Chaucer complies with the boring story of Melibee.
After the tale of Melibee, the Host turns to the merry Monk and demands a story that he confidently expects to be a jovial and happy tale. Instead, the Monk relates a series of tales in which tragedy befalls everyone. The Knight joins in with the Host in proclaiming that the Monk's tales are too much to bear and requests a merry tale. But the Monk refuses, and the Host turns to the Nun's Priest and calls for a tale. Thus the Nun's Priest relates the tale of the barnyard rooster, Chaunticleer, his lady, and a fox. The Second Nun then offers a tale that befits her station — a retelling of the events in the life of St. Cecilia.
Suddenly, two men approach the pilgrims. One is a canon; the other his yeoman (servant). The Host welcomes them and asks whether either has a tale to tell. The Canon's Yeoman answers that his master has many strange tales filled with mirth and laughter, yet when he begins to tell of their life and actions, the Canon slips away embarrassed and frightened.
As the party nears Canterbury, the Host demands a story from the Manciple, who tells of a white crow that can sing and talk. Finally, the Host turns to the last of the group, the Parson, and bids him to tell his tale. The Parson agrees and proceeds with a sermon. The Tales end with Chaucer's retraction.