- The General Prologue begins with a description of how April's showers cause flowers to bloom, crops to grow, birds to sing, and people to want to make pilgrimages – journeys to holy places. In England, people especially like to go to Canterbury to pray at the shrine of a holy saint who healed them when they were sick.
- The narrator tells how, in that season, he is at a tavern in Southwark getting ready to make his pilgrimage to Canterbury. There, he meets a large group of pilgrims, also going to Canterbury. Soon, he has spoken with each of them and has become a member of their group, or 'felaweshipe.'
- The narrator describes the appearance and behavior of all of the pilgrims in great detail. (For a detailed description of each of the character's portraits, see the 'Characters' section.)
- The narrator concludes his description of the pilgrims with his promise to describe what happens to them that evening and on their pilgrimage. He asks the reader's forgiveness if he gives offense, claiming as his excuse his obligation to repeat the pilgrim's words and deeds exactly, even if they are rude.
- The host serves dinner.
- The narrator describes the host. (For a detailed description of the Host's portrait, see the "Characters" section.)
- The Host praises the group of pilgrims as being the most merry he's seen in a long time. He expresses his desire to "do them mirth," or make them happy. He tells the pilgrims that, if they agree to do as he says, they will have lots of fun on their way to Canterbury.
- The pilgrims confer amongst themselves and quickly agree to do as the host says.
- The host proposes that each pilgrim tell two tales on the way to Canterbury, and two on the way back. Whoever tells the best tale as judged by the Host wins a free dinner when they arrive back at his tavern. Whoever expresses disagreement with the Host's judgment has to pay for the entire cost of the pilgrimage.
- The pilgrims swear oaths to abide by the rules of the game, and to submit to the authority of the Host.
- The pilgrims go to bed.
- In the morning, the Host wakes the pilgrims and they start down the road.
- At the watering hole of Saint Thomas, the Host reminds the pilgrims of their agreement and proposes that they draw straws to decide who goes first.
- The Knight draws the shortest straw, and so begins the tale-telling contest.