It begins in April--does it end before winter
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While the journey appears rather short today, in Chaucer's time the distance would take several days to travel. Because of the number of place references in the tales some scholars believe that it took three days with only a few stops, while others think that it is closer to four or five days.
While it is true that we can't exactly pinpoint the amount of time that the pilgrims traveled because not all the tales are finished, it is possible to make a logical assumption based on geographic references.