Harry Bailey gives the pilgrims the challenge of telling a story on the journey to Canterbury and back. Each pilgrim must share two stories on the way, and two stories on the way back, for a total of four tales.
Harry Bailey was the host of the Tabard Inn where the pilgrims in The Canterbury Tales gather before embarking on their journey to Canterbury.
The Tabard was an inn in Southwark, owned by Harry Bailly, where the Pilgrims in the Canterbury Tales stayed. (Harry Bailly decides he enjoys their company so much he will go with them on their pilgrimage.)
Each of the pilgrims will tell two stories on the way to Canterbury, and two more on the road home. Whichever pilgrim is considered the best storyteller will then have a free meal at Harry Bailey's inn, to be paid for by the other pilgrims.
The Host, Harry Bailey, does not have to tell stories in The Canterbury Tales. He is the one who proposes the storytelling competition among the pilgrims and serves as the master of ceremonies throughout the tales.
In "The Canterbury Tales," Harry Bailey proposes that each pilgrim tell two tales on the way to Canterbury and two on the way back. After the trip was over, it is assumed that Harry Bailey returned to his inn, where he likely continued to run his business and host guests.
The name of the man who organized the pilgrimage and mediated the tale-telling contest in Geoffrey Chaucer's "The Canterbury Tales" is Harry Bailey, also known as Our Hoste. He was the owner of the Tabard Inn in Southwark, where the pilgrims stayed before embarking on their journey to Canterbury Cathedral.
The Host, Harry Bailey, proposes the storytelling challenge to make the pilgrimage more enjoyable. Each pilgrim is to tell four stories on the way to Canterbury and four on the way back, with the best storyteller to be rewarded with a free meal.
The pilgrims agree to set up the Host, Harry Bailey, as judge over themselves in the Prologue of "The Canterbury Tales." He proposes a storytelling competition to pass the time on their journey to Canterbury, with the best tale winning a free meal at the end of the trip.
Geoffrey Chaucer, an English poet and author, is credited with coming up with the idea of telling stories in "The Canterbury Tales". The collection of stories is set within a framing narrative of a group of pilgrims traveling to Canterbury, each sharing a tale as part of a storytelling competition.
Harry Bailey - the publican of the Tabard Inn at Southwark (where the story begins) offers to join the pilgrimage to Canterbury. On the way out, and then again on the way home, each pilgrim will tell two stories. The best storyteller will be rewarded with a free dinner. Harry Bailey will be the judge of the stories.
The purpose of the pilgrims telling tales during their journey in Geoffrey Chaucer's "The Canterbury Tales" is to pass the time and entertain each other. By sharing stories, the pilgrims engage in friendly competition, reveal their personalities and beliefs, and provide insight into medieval society and human nature. Through these tales, Chaucer explores themes of love, morality, and social class.
In the General Prologue, Chaucer has already checked in, when he says that 29 more arrived in a company. He then names 30 more. With Chaucer and the Host, 32 set out. They are joined by the Canon's Yeoman to make a group of 33 at the end, a suitable number of some religious significance (years of Christ's life, e.g.) Note that 29 is also of some significance, since St. Thomas a Becket's feast day is Dec. 29. Why the error? Probably since Chaucer the Narrator is always making quick judgments, which the reader has to take with a grain of salt. This is Chaucer the Poet's ironic way of first indicating this to us. For more details, see Caroline Eckhardt's "The Number of Chaucer's Pilgrims: A Review and Reappraisal" in The Yearbook of English Studies, Vol 5 (1975), pp. 1-18.