The Canterbury Tales begins with the introduction of each of the pilgrims making their journey to Canterbury to the shrine of Thomas a Becket. These pilgrims include a Knight, his son the Squire, the Knight's Yeoman, a Prioress, a Second Nun, a Monk, a Friar, a Merchant, a Clerk, a Man of Law, a Franklin, a Weaver, a Dyer, a Carpenter, a Tapestry-Maker, a Haberdasher, a Cook, a Shipman, a Physician, a Parson, a Miller, a Manciple, a Reeve, a Summoner, a Pardoner, the Wife of Bath, and Chaucer himself. Congregating at the Tabard Inn, the pilgrims decide to tell stories to pass their time on the way to Canterbury. The Host of the Tabard Inn sets the rules for the tales. Each of the pilgrims will tell two stories on the way to Canterbury, and two stories on the return trip. The Host will decide whose tale is best for meaningfulness and for fun. They decide to draw lots to see who will tell the first tale, and the Knight receives the honor.
The Knight's Tale is a tale about two knights, Arcite and Palamon, who are captured in battle and imprisoned in Athens under the order of King Theseus. While imprisoned in a tower, both see Emelye, the sister of Queen Hippolyta, and fall instantly in love with her. Both knights eventually leave prison separately: a friend of Arcite begs Theseus to release him, while Palamon later escapes. Arcite returns to the Athenian court disguised as a servant, and when Palamon escapes he suddenly finds Arcite. They fight over Emelye, but their fight is stopped when Theseus finds them. Theseus sets the rules for a duel between the two knights for Emelye's affection, and each raise an army for a battle a year from that date. Before the battle, Arcite prays to Mars for victory in battle, Emelye prays to Diana that she may marry happily, and Palamon prays to Venus to have Emelye as his wife. All three gods hear their prayers and argue over whose should get precedence, but Saturn decides to mediate. During their battle, Arcite indeed is victorious, but as soon as he is crowned victor, he is killed. Before he dies, he reconciles with Palamon and tells him that he deserves to marry Emelye. Palamon and Emelye marry.
When the Knight finishes his tale, everybody is pleased with its honorable qualities, but the drunken Miller insists that he shall tell the next tale. The Miller's Tale, in many ways a version of the Knight’s, is a comic table in which Nicholas, a student who lives with John the carpenter and his much younger wife, Alison, falls in love with Alison. Another man, the courtly romantic Absolon, also falls in love with Alison. Nicholas contrives to sleep with Alison by telling John that a flood equal to Noah's flood will come soon, and the only way that he, Nicholas and Alison will survive is by staying in separate kneading tubs placed on the roof of houses, out of sight of all. While John remained in this kneading tub, Nicholas and Alison leave to have sex, but are interrupted by Absolon, singing to Alison at her bedroom window. She told him to close his eyes and he would receive a kiss. He did so, and she pulled down her pants so that he could kiss her arse. The humiliated Absolon got a hot iron from a blacksmith and returned to Alison. This time, Nicholas tried the same trick, and Absolon branded his backside. Nicholas shouted for water, awakening John, who was asleep on the roof. Thinking the flood had come, he cut the rope and came crashing through the floor of his house, landing in the cellar.
The pilgrims laughed heartily at this tale, but Oswald the Reeve takes offense, thinking that the Miller meant to disparage carpenters. In response, The Reeve's Tale tells the story of a dishonest Miller, Symkyn, who repeatedly cheated his clients, which included a Cambridge college. Two Cambridge students, Aleyn and John, went to the miller to buy meal and corn, but while they were occupied Symkyn let their horses run free and stole their corn. They were forced to stay with Symkyn for the night. That night, Aleyn seduced the miller's daughter, Molly, while John seduced the miller's wife. Thanks to a huge confusion of whose bed is who in the dark, Aleyn tells Symkyn of his exploits, thinking he is John: and the two fight. The miller's wife, awaking and thinking the devil had visited her, hit Symkyn over the head with a staff, knocking him unconscious, and the two students escaped with the corn that Symkyn had stolen.
The Cook's Tale was intended to follow the Reeve's Tale, but this tale only exists as a fragment. Following this tale is the Man of Law's Tale, which tells the story of Constance, the daughter of a Roman emperor who becomes engaged to the Sultan of Syria on the condition that he converts to Christianity. Angered by his order to convert his country from Islam, the mother of the Sultan assassinates her son and Constance barely escapes. She is sent on a ship that lands in Britain, where she is taken in by the warden of a nearby castle and his wife, Dame Hermengild. Both of them soon convert to Christianity upon meeting her. A young knight fell in love with Constance, but when she refused him, he murdered Dame Hermengild and attempted to frame Constance. However, when King Alla made the knight swear on the Bible that Constance murdered Hermengild, his eyes burst. Constance marries King Alla and they have a son, Mauritius, who is born when Alla is at war in Scotland. Lady Donegild contrives to have Constance banished by intercepting the letters between Alla and Constance and replacing them with false ones. Constance is thus sent away again, and on her voyage her ship comes across a Roman ship. A senator returns her to Rome, where nobody realizes that she is the daughter of the emperor. Eventually, King Alla makes a pilgrimage to Rome, where he meets Constance once more, and the Roman emperor realizes that Mauritius is his grandson and names him heir to the throne.
The Wife of Bath begins her tale with a long dissertation on marriage in which she recounts each of her five husbands. Her first three husbands were old men whom she would hector into providing for her, using guilt and refusal of sexual favors. However, the final two husbands were younger men, more difficult to handle. The final husband, Jankin, was a twenty-year-old, half the Wife of Bath's age. He was more trouble, as he refused to let the Wife of Bath dominate him and often read literature that proposed that women be submissive. When she tore a page out of one of his books, Jankin struck her, causing her to be deaf in one ear. However, he felt so guilty at his actions that from that point in the marriage, he was totally submissive to her and the two remained happy. The Wife of Bath's Tale is itself a story of marriage dynamic. It tells the tale of a knight who, as punishment for raping a young woman, is sentenced to death. However, he is spared by the queen, who will grant him freedom if he can answer the question "what do women want?" The knight cannot find a satisfactory answer until he meets an old crone, who promises to tell him the answer if he marries her. He agrees, and receives his freedom when he tells the queen that women want sovereignty over their husbands. However, the knight is dissatisfied that he must marry the old, low-born hag. She therefore tells him that he can have her as a wife either old and ugly yet submissive, or young and beautiful yet dominant. He chooses to have her as a young woman, and although she had authority in marriage the two were completely happy from that point.
The Friar asks to tell the next tale, and asks for pardon from the Summoner, for he will tell a tale that exposes the fraud of that profession. The Friar's Tale tells about a wicked summoner who, while delivering summons for the church court, comes across a traveling yeoman who eventually reveals himself to be the devil himself. The two share trade secrets, and the devil tells him that they will meet again in hell if the summoner continues to pursue his trade. The summoner visits an old woman and issues her a summons, then offers to accept a bribe as a payment to prevent her excommunication. The old woman believes that she is without sin and curses the summoner. The devil then appears and casts the summoner into hell.
The Summoner was enraged by the Friar's Tale. Before he begins his tale, he tells a short anecdote: a friar visited hell and was surprised to see that there were no other friars. The angel who was with him then lifted up Satan's tail and thousands of friars swarmed out from his arse. The Summoner's Tale is an equally vitriolic attack on friars. It tells of a friar who stays with an innkeeper and his wife and bothers them about not contributing enough to the church and not attending recently. When the innkeeper tells him that he was not recently in church because he has been ill and his infant daughter recently died, the friar attempted to placate him and then asked for donations once more. Thomas the innkeeper promised to give the friar a “gift” and gives him a loud fart.
The Clerk, an Oxford student who has remained quiet throughout the journey, tells the next tale on the orders of the Host. The Clerk's Tale recounts a story about Walter, an Italian marquis who finally decides to take a wife after the people of his province object to his longtime status as a bachelor. Walter marries Griselde, a low-born but amazingly virtuous woman whom everybody loves. However, Walter decides to test her devotion. When their first child, a daughter, is born, Walter tells her that his people are unhappy and wish for the child's death. He takes away the child, presumably to be murdered, but instead sends it to his sister to be raised. He does the same with their next child, a son. Finally, Walter tells Griselde that the pope demands that he divorce her. He sends her away from his home. Each of these tragedies Griselde accepts with great patience. Walter soon decides to make amends, and sends for his two children. He tells Griselde that he will marry again, and introduces her to the presumed bride, whom he then reveals is their daughter. The family is reunited once more. The Clerk ends with the advice that women should strive to be as steadfast as Griselde, even if facing such adversity is unlikely and perhaps impossible.
The Merchant praises Griselde for her steadfast character, but claims that his wife is far different from the virtuous woman of the Clerk's story. He instead tells a tale of an unfaithful wife. The Merchant's Tale tells a story of January, an elderly blind knight who decides to marry a young woman, despite the objections of his brother, Placebo. January marries the young and beautiful May, who soon becomes dissatisfied with his sexual attentions to her and decides to have an affair with his squire, Damian, who has secretly wooed her by signs and tokens. When January and May are in their garden, May sneaks away to have sex with Damian. The gods Pluto and Proserpina come upon Damian and May and Pluto restores January's sight so that he may see what his wife is doing. When January sees what is occurring, May tells him not to believe his eyes – they are recovering from the blindness - and he believes her: leading to an on-the-surface happy ending.
The Squire tells the next tale, which is incomplete. The Squire's Tale begins with a mysterious knight arriving at the court of Tartary. This knight gives King Cambyuskan a mechanical horse that can transport him anywhere around the globe and return him within a day. Further, he gives Canacee, the daughter of Cambyuskan, a mirror that can discern honesty and a ring that allows the wearer to know the language of animals and the healing properties of all herbs. Canacee uses this ring to aid a bird who has been rejected in love, but the tale then abruptly ends.
The Franklin's Tale that follows tells of the marriage between the knight Arviragus and his wife, Dorigen. When Arviragus travels on a military expedition, Dorigen laments his absence and fears that, when he returns, his ship will be wrecked upon the rocks off the shore. A young man, Aurelius, falls in love with her, but she refuses to return his favors. She agrees to have an affair with Aurelius only on the condition that he find a way to remove the rocks from the shore, a task she believes impossible. Aurelius pays a scholar who creates the illusion that the rocks have disappeared, while Arviragus returns. Dorigen admits to her husband the promise that she has made, and Arviragus tells her that she must fulfill that promise. He sends her to have an affair with Aurelius, but he realizes the pain that it would cause Dorigen and does not make her fulfill the promise. The student in turn absolves Aurelius of his debt. The tale ends with the question: which of these men behaved most generously and nobly?
The Physician's Tale that follows tells of Virginius, a respected Roman knight whose daughter, Virginia, was an incomparable beauty. Appius, the judge who governed his town, lusted after Virginia and collaborated with Claudius, who claimed in court that Virginia was his slave and Virginius had stolen her. Appius orders that Virginia be handed over to him. Virginius, knowing that Appius and Claudius did this in order to rape his daughter, instead gave her a choice between death or dishonor. She chooses death, and Virginius chops off his daughter's head, which he brings to Appius and Claudius. The people were so shocked by this that they realized that Appius and Claudius were frauds. Appius was jailed and committed suicide, while Claudius was banished.
The Pardoner prefaces his tale with an elaborate confession about the deceptive nature of his profession. He tells the secrets of his trade, including the presentation of useless items as saints' relics. The Pardoner's Tale concerns three rioters who search for Death to vanquish him. They find an old man who tells them that they may find Death under a nearby tree, but under this tree they only find a large fortune. Two of the rioters send the third into town to purchase food and drink for the night (when they intend to escape with their fortune) and while he is gone they plan to murder him. The third rioter poisons the drink, intending to take all of the money for himself. When he returns, the two rioters stab him, then drink the poisoned wine and die themselves. The three rioters thus find Death in the form of avarice. The Pardoner ends his tale with a diatribe against sin, imploring the travelers to pay him for pardons, and be absolved, but the Host berates him scatalogically into silence.
The next story, The Shipman's Tale, is the story of a thrifty merchant and his wife. The wife tells a monk, the merchant’s close friend, that she is unhappy in her marriage, and asks if she might borrow a hundred francs of his. In return for the loan, she agrees, she will sleep with him. The monk then borrows the money from the merchant himself, sleeps with his wife, and pays her her husband’s money. When the merchant asks for his money back, the monk tells him it he gave it to the wife: and when the merchant confronts his wife, the wife simply tells him that she will repay the debt to her husband in bed.
The Prioress' Tale tells the story of a young Christian child who lived in a town in Asia that was dominated by a vicious Jewish population. One child learned the “Alma redemptoris”, a song praising the Virgin Mary, and traveled home from school singing it. The Jews, angry at his behavior, took the child and slit his throat, leaving him in a cesspit to die. The boy's mother searched frantically for her son. When she found him, he was not yet dead, for the Virgin Mary had placed a grain on his tongue that would allow him to speak until it was removed. When this was removed, the boy passed on to heaven. The story ends with a lament for the young boy and a curse for the Jews who perpetrated the heinous crime.
Chaucer himself tells the next tale, The Tale of Sir Thopas, a florid and fantastical poem in rhyming couplets that serves only to annoy the other pilgrims. The Host interrupts Chaucer shortly into this tale, and tells him to tell another. Chaucer then tells The Tale of Melibee, one of two tales that is in prose (the other is the Parson’s Tale). This tale is about Melibee, a powerful ruler whose enemies attack his family. When deciding whether to declare war on his enemies, Prudence, his wife, advises him to remain merciful, and they engage in a long debate over the appropriate course of action. Melibee finally gives his enemies the option: they can receive a sentence either from him or from his wife. They submit to Melibee's judgment, and he intends to disinherit and banish the perpetrators. However, he eventually submits to his wife's plea for mercy.
The Monk's Tale is not a narrative tale at all, but instead an account of various historical and literary figures who experience a fall from grace. These include Adam, Samson, Hercules, King Pedro of Spain, Bernabo Visconti, Nero, Julius Caesar, and Croesus. The Knight interrupts the Monk's Tale, finding his listing of historical tragedies monotonous and depressing, and is backed up by the Host.
The Nun's Priest's Tale tells the story of the rooster Chaunticleer and the hen Pertelote. Chaunticleer was ill one night and had a disturbing dream that he was chased by a fox. He feared this dream was prophetic, but Pertelote assured him that his dream merely stemmed from his imbalanced humours and that he should find herbs to cure himself. Chaunticleer insisted that dreams are signifiers, but finally agreed with his wife. However, Chaunticleer is indeed chased by a fox, and carried off – but is saved when he tricks the fox into opening his mouth, allowing Chaunticleer to fly away.
Chaucer follows this with The Second Nun's Tale. This tale is a biography of Saint Cecilia, who converts her husband and brother to Christianity during the time of the Roman empire, when Christian beliefs were illegal. Her brother and husband are executed for their beliefs, and she herself is cut three times with a sword during her execution, but does not immediately die. Rather, she lingers on for several more days, during which time she orders that her property be distributed to the poor. Upon her death Pope Urban declared her a saint.
After the Second Nun finishes her tale, a Canon (alchemist) and his Yeoman join the band of travelers. The Canon had heard how they were telling tales, and wished to join them. The Yeoman speaks incessantly about the Canon, praising him hugely, but then retracts his praise, annoying the Canon, who suddenly departs. The Yeoman therefore decides to tell a tale about a duplicitous Canon: not, he says, his master. The Canon's Yeoman's Tale is a story of the work of a canon and the means by which they defraud people by making them think that they can duplicate money.
The Host tells the Cook to tell the next tale, but he is too drunk to coherently tell one. The Manciple therefore tells a tale. The Manciple's Tale is the story of how Phoebus, when he assumed mortal form, was a jealous husband. He monitored his wife closely, fearing that she would be unfaithful. Phoebus had a white crow that could speak the language of humans and could sing beautiful. When the white crow learns that Phoebus' wife was unfaithful, Phoebus plucked him of his feathers and threw him out of doors. According to the Manciple, this explains why crows are black and can only sing in an unpleasant tone.
The Parson tells the final tale. The Parson's Tale is not a narrative tale at all, however, but rather an extended sermon on the nature of sin and the three parts necessary for forgiveness: contrition, confession, and satisfaction. The tale gives examples of the seven deadly sins and explains them, and also details what is necessary for redemption. Chaucer ends the tales with a retraction, asking those who were offended by the tales to blame his rough manner and lack of education, for his intentions were not immoral, while asking those who found something redeemable in the tales to give credit to Christ.