A Storytelling Contest That Never Finished: Chaucer's Canterbury Tales for New Readers

For beginners, The Canterbury Tales is easiest to picture as a road trip with a game attached. A mixed group of medieval pilgrims sets out from London to visit the shrine of Saint Thomas Becket at Canterbury Cathedral, and to pass the time they hold a storytelling contest. Geoffrey Chaucer wrote the work in Middle English between 1387 and 1400, and it contains twenty-four stories, mostly in verse. The tales range from noble romance to dirty jokes, sermons and fables, and each one tells you as much about the person telling it as about its plot. The collection was never finished: the plan in the opening section promises far more stories than Chaucer lived to write. This guide explains how the frame works, who Chaucer was, which tales to read first, what the book is really about and why it matters for the English language itself.

What kind of book is it?

The Canterbury Tales is a frame narrative: one outer story holds many inner stories. The outer story is the pilgrimage and the contest; the inner stories are the tales the pilgrims tell. Frame collections were already a long-established form in the Middle Ages, and Chaucer's has more parallels with Giovanni Boccaccio's Decameron, in which young Florentines escaping the Black Death tell each other stories, than with any other work. Yet no earlier work is known to have set a collection of tales among pilgrims on a pilgrimage, and most story collections stuck to a single theme, often a religious one. Chaucer's stands out for its sheer variety.

The book is widely regarded as Chaucer's masterpiece and one of the most important works of English literature. It also had a major effect on the development of English writing, and may have helped make English, rather than French or Latin, an accepted language for serious literature.

Who was Chaucer, and why is the work unfinished?

Geoffrey Chaucer was born around 1343 and died on 25 October 1400. He is often called the father of English literature, or of English poetry, and he was the first writer buried in what later became Poets' Corner in Westminster Abbey. He was not a full-time poet. He worked as a courtier, diplomat and civil servant, served in Parliament, and wrote a scientific treatise on the astrolabe for his ten-year-old son. As a young man he fought in the Hundred Years' War and was captured during the siege of Reims in 1360; the king paid his ransom. He began The Canterbury Tales in the years when he was a customs official and then Clerk of the King's Works, which may explain how well he knew people from every level of society.

The General Prologue introduces about thirty pilgrims and says each will tell two tales on the way to Canterbury and two on the way back, which would have meant roughly 120 stories. Most scholars think the work was still incomplete when Chaucer died. There is also no agreement on the order he intended. The tales survive in 84 manuscripts and four early printed editions, none in Chaucer's own hand, and modern editions usually group them into ten "Fragments" whose sequence still varies. So what we read is less a finished book than a large, brilliant work in progress.

How the frame works

The pilgrims gather at an inn, and the innkeeper, the Host Harry Bailey, introduces them and proposes the contest. The inn was the Tabard in Southwark, on the south side of the Thames, and a blue plaque now marks its site. The winner's prize is a free dinner, an idea that echoes real 14th-century storytelling and song contests in England. Chaucer himself rides along as one of the pilgrims and even tells two tales of his own.

What makes the frame lively is that the General Prologue describes the storytellers, not the stories, so the structure depends on the characters. The Knight, the most respected pilgrim, goes first, which suggests that everyone will speak in order of rank. Then the drunken Miller barges in and insists on telling his tale next, and from that moment the contest becomes a free-for-all among all classes. Pilgrims interrupt, insult and answer each other, and some tales are told specifically to "quit", or get back at, a previous teller.

Four tales to start with

The Knight's Tale opens the contest. Two cousins and knights, Palamon and Arcite, are imprisoned in Athens, and from their cell window both fall in love with the same young woman, Emelye, picking flowers in the garden below. Their friendship collapses into rivalry. It is a chivalric romance based on an epic by Boccaccio, full of courtly love and moral dilemmas.

The Miller's Tale follows immediately and turns the Knight's noble rivalry upside down. It is a rowdy, bawdy comic story, a type called a fabliau, also about two men competing for a woman, and it is designed to annoy the Knight and amuse everyone else. Putting the two side by side is Chaucer's joke: same basic plot, opposite worlds.

The Wife of Bath's Tale comes from one of Chaucer's most vivid characters, a woman who has married several times and defends her right to do so in a prologue twice as long as her story. Her tale is set in King Arthur's time. A knight who has committed a terrible crime is told he can save his life if, within a year and a day, he discovers what women most desire. An ugly old woman gives him the answer, sovereignty over their husbands and lovers, in exchange for a promise that turns out to be marriage.

The Pardoner's Tale is a dark moral fable. Three young men set out to kill Death. An old man tells them they will find him under a nearby tree; there they discover a pile of treasure instead, and out of greed they murder one another. The twist is that the teller, a seller of church pardons, openly admits that he cheats people, and his theme is radix malorum est cupiditas, "greed is the root of evil".

The pilgrims as a portrait of a society

Chaucer's pilgrims come from almost every part of late medieval English society, which people at the time divided into three estates: those who pray, those who fight and those who work. There are a Knight and his Squire, churchmen such as the Monk, the Prioress and the Parson, and working people such as the Miller, the Cook and the Reeve. Chaucer's descriptions often sound like compliments on the surface but quietly criticise the pilgrims, and readers who know medieval society can detect subtle satire everywhere.

The Church gets some of the sharpest treatment. The Pardoner and the Summoner, two officials who handled the Church's powers of forgiveness and punishment, are shown as greedy and corrupt, while the Monk and the Prioress dress expensively and live in comfort far from the ideals of their orders. This was a turbulent time: after the Black Death many Europeans began to question the Church's authority, and the Tales even mention the reform movement known as Lollardy and the Peasants' Revolt of 1381.

What the book is really about

Because so many voices speak, the book never settles on one truth. Each genre sees the world differently: the comic fabliau hardly notices God, the saint's life barely notices the physical world, the sermon insists on morality, and the romance puts human feeling first. The result is an atmosphere of testing and comparison rather than a single message. At the same time, the pilgrimage that ties every story together can be read as an image of people striving towards heaven despite their weaknesses and disagreements. The work ends with Chaucer's "Retraction", a short prayer in which he asks forgiveness for those of his writings that dwell on worldly vanities.

Why it matters for English

Chaucer wrote in a London dialect of late Middle English, which you can partly read today but which sounded very different. He pronounced many final -e endings, and in a word such as knight both the k and the gh were sounded, because the Great Vowel Shift had not yet happened. He helped make English respectable for literature at a time when French and Latin dominated, and almost two thousand English words, such as amble, altercation and arrogant, are first recorded in his manuscripts. About seventy-five years after his death, William Caxton chose the Tales as one of the first books printed in England, in an edition of 1476.

The stories have been retold ever since, from Shakespeare and Fletcher's The Two Noble Kinsmen, a version of the Knight's Tale, to Pasolini's 1972 film and Zadie Smith's 2021 play The Wife of Willesden. To begin, read the General Prologue in a modern translation, then the Knight's and Miller's tales together, then the Wife of Bath and the Pardoner. Afterwards, try the first lines of the Prologue in the original Middle English, slowly and aloud.

Learn with The Canterbury Tales: English words and phrases

Word or phrase	Meaning	Example
pilgrimage	a journey to a sacred or meaningful place	Visiting the stadium was a pilgrimage for him.
to amble	to walk slowly and comfortably	We ambled along the river after lunch.
altercation	a noisy argument	There was an altercation at the ticket desk.
greed is the root of all evil	wanting too much leads to wrongdoing	The film shows that greed is the root of all evil.
to tell tales	to report someone's wrongdoing; to gossip	Don't tell tales about your classmates.

Try this: Imagine you are on a long bus trip with strangers. Write three English sentences describing one fellow passenger and the kind of story they would tell, using "to amble" and "pilgrimage".