In the General Prologue to The Canterbury Tales, Chaucer is quite explicit regarding the time of year in which the pilgrimage occurs:
Whan that Aprill with his shoures soote / The droghte of March hath perced to the roote, / And bathed every veyne in swich licour / Of which vertu engendred is the flour; / Whan Zephirus eek with his sweete breath.... (GP:1-5)
So, if there is not much doubt with respect to the timing of the pilgrimage—sometime in early April when spring is well underway. The interesting question is, "Why in spring?"
Over the years, Chaucer scholars have written reams about the pilgrimage in the General Prologue as a "framing" narrative—that is, the form that allows each pilgrim to tell his or her story and gives Chaucer a familiar vehicle to represent people from all ranks within medieval English society. In addition, a pilgrimage to Thomas a'...
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Becket's shrine at Canterbury was an important way of showing piety, and pilgrims were a common sight from all points of England on their way to Canterbury.
Chaucer most likely uses the beginning of spring for at least two reasons, the first of which is the association of spring with the renewal of life. As Chaucer puts it, like birds whose sexual desires are awakening as spring advances, pilgrims get the urge to make a journey:
And smale fowles maken melodye, / That slepen all the nyght with open ye / So priketh hem nature in hir corages / Thanne longen folk to goon on pilgrimages. (GP: 9-12)
In other words, birds are incited by Nature in a sexual way, and pilgrims are also incited to take some action—not necessarily sexual, but active nevertheless. Several Chaucerian critics have argued that Chaucer's setting of the pilgrimage in spring is his subtle way of linking the pilgrimage to non-pious motives on the part of the pilgrims. This argument has some merit, considering that the pilgrimage begins at a tavern in Southwark, an area of London known not for its piety but its risqué entertainments. (See Sebastian Sobieski, "Pilgrimage and Travel," A New Companion to Chaucer, 2019.)
Another likely possibility for the timing is simply that spring is not only the archetypal period of nature's renewal but also is linked to the resurrection (renewal) of Christ. Given Chaucer's genial way of joining otherwise disparate things—the pilgrims themselves, for example—he may have used spring to show(1) the renewal of life and sexuality among people and animals; (2) that after harsh winters, travel in spring becomes practical and even enjoyable; and (3) that the piety associated with pilgrimage reflects Christ's renewal on the cross, which would have been celebrated in medieval England about two weeks before the pilgrimage begins.
If we reflect on the complex nature of the pilgrims and their tales, we can reasonably conclude that Chaucer's choice of spring for the pilgrimage is the result of an equally complex pattern created by religious motives, the influence of nature's regeneration, and practicalities, like good roads and weather.