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As April comes, the narrator begins a pilgrimage to Canterbury from the Tabard Inn at Southwerk. Twenty-nine people make the pilgrimage toward Canterbury and the narrator describes them in turn. The pilgrims are listed in relative order of status, thus the first character is the Knight. Chaucer describes the knight as a worthy man who had fought in the Crusades. With him is a Squire, the son of the Knight and a 'lusty bachelor' of twenty. The Knight has a second servant, a Yeoman. There is also a Prioress, shy and polite. She is prim and proper, sympathetic and well-mannered. The Prioress wears a broach with the inscription "All things are subject unto love." With the Prioress is her secretary (the Second Nun) and a Monk. The monk is a robust and masculine man who loves to hunt. The Friar, Hubert, is an immoral man more concerned with making profit than converting men from sin. The Merchant from Flanders is a pompous man who speaks endlessly on how profits may be increased. He seems grave, yet there is no better man, according to the narrator. The Clerk follows the Merchant. As an Oxford student without employment, he is impoverished and wears threadbare clothes. The Man of Law is a man who deserves to be held in awe. He knows the law to the letter and gives the impression that he is far busier than he actually is. A Franklin travels with him. He is a man who lives in comfort and is interested simply in pleasure, particularly culinary delight. There are also five guildsmen: a Weaver, a Dyer, a Carpenter, a Tapestry-maker and a Haberdasher. With them they bring a Cook. A Shipman is the next traveler, who comes from the port of Dartmouth, and with him a Physician. The Wife of Bath is next; she is a weaver who wears bright red clothing. She has been married five times (and had several companions as a youth). The Parson is an honorable, decent man who cares for his congregation and adheres to the teachings of Christ. With him is his brother, a Plowman, who is equally kind. The final travelers are a Miller, a Manciple, a Reeve, a Summoner and a Pardoner. The Miller is a large man with an imposing physique. The Manciple is from a lawyers' college and knows every legal maneuver. The Reeve is a slender man with a fiery temper.
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In the General Prologue, Chaucer sets up the general structure of the tales and introduces each of the characters who will tell the tales. The characters who tell each of the tales are as important as the characters in the tales that they tell; a significant portion of the action of the Canterbury Tales takes place within the prologues to each of the tales. The General Prologue in essence serves as a guide for the tales, giving some explanation for the motivation behind each of the tales each character tells.
The introductory imagery of the General Prologue mixes the spiritual with the secular and moves between each form with relative ease. The Canterbury Tales begins with the famous lines "Whanne that Aprill with his shoures soote / The droghte of March hath perced to the roote," setting up imagery of spring and regeneration. Yet he does not continue with the logical outcome of this springtime imagery. Instead of conforming to the cliché "in springtime a young man's fancy turns to love," Chaucer veers into more spiritual territory. In springtime these travelers make a religious pilgrimage to Canterbury. Yet Chaucer is equally uninterested in the religious details of this journey, and keeps the beginning passages of the General Prologue focused on nature and not on the human society with which the travelers will deal.
Chaucer gives relatively straightforward descriptions of the characters and has some inclination to show their best qualities. Chaucer describes virtually each pilgrimage as an exemplar a number of these pilgrims are described as 'perfect' in some way or another, most often in their craft. Furthermore, these pilgrims exist almost entirely in terms of their profession. Chaucer gives only a few of them character names, and these emerge only in terms of conversation between the characters during each tale's prologue, and not in Chaucer's description in the General Prologue.
Yet even within these descriptions he allows for subtle criticism and sly wit. The description of the Prioress in particular, is overtly flattering yet masquerades a sharp criticism of her foolish sentimentality and oppressive attention to manners. Although she strives to be polite and refined, she spoke French "after the school of Stratford-at-Bow," the vulgar rural pronunciation compared to elite Parisian French. Furthermore, she weeps at the mere sight of a dead mouse, a gross overreaction to a small tragedy.
The descriptions of the upper members of the clergy deserve special note in context of the tales. Each of the clergymen defy traditional expectations; the Monk is a rough laborer, while the Friar is resolutely immoral. Chaucer lists the various sins of the Friar: he sells pardon from sin for a price, seduces women who ask for pardons, and spends more time in bars than he does aiding the poor. His concern for profit is a stark contrast with that of the Merchant. While the Merchant merely dispenses advice on how to attain profit, it is the Friar who applies his entire existence to its pursuit. The Friar further contrasts with the later description of the Parson, a man who performs his duties honorably and cares for his congregation. In his description of the Parson, Chaucer lists the various admirable qualities, none of which are held by the Friar.
The description of the Merchant is also notable, for it shows the disparity between how the narrator overtly appraises a character and what he describes. After listing a number of unflattering qualities in the Merchant, the narrator still judges him to be a fine man; in these descriptions, the details and anecdotes are far more important in defining character than the final stated opinion of the narrator.
Chaucer indulges in comic criticism in his portrait of the Clerk. This Oxford student, however educated, is not worldly enough for any normal employment. He has studied only impractical knowledge, and even carries among his few possessions several volumes of Aristotle.
Most of the travelers engaged in a profession receive little description; as the travelers move down the social scale Chaucer gives them less and less detailed descriptions. The Wife of Bath is the most significant of the travelers low on the social scale. Chaucer describes her as lewd and boisterous. Her clothing, all variations of bright red, is ostentatious, meant to attract attention from others. Chaucer even indicates that she is quite promiscuous she has been married five times and had an undetermined number of lovers. The other traveler who merits a lengthy description is the Pardoner. He has a very effeminate manner, with a high voice and soft features. Chaucer even compares him to a gelding (a castrated horse) or a mare, which may be a subtle comment on his sexuality.
The prologue sets up the general design of the Canterbury Tales. Each character will tell four tales during the journey, leading to a grand total of 116 tales. Chaucer never completed all of the tales, starting only about one fourth of the possible stories, not all of which remain in their entirety. Some of the stories that remain are only fragments which have either been lost or were never completed by the author.
When the travelers draw lots to decide who will tell the first story, it is the Knight who has the first choice. Although the order is supposedly random, the Knight draws the first lot and thus randomly receives the rank appropriate to his status, which indicates that the Host may have fixed the lots in order to curry favor with the Knight.