Final answer:
Each pilgrim in 'The Canterbury Tales' is expected to tell four stories according to Harry Bailey, two on the way to Canterbury and two on the way back.
Step-by-step explanation:
According to Harry Bailey in Geoffrey Chaucer's The Canterbury Tales, each pilgrim is expected to tell two stories on the way to Canterbury and two more on the way back. Therefore, the total number of stories each pilgrim would tell is four. Harry Bailey, who is the host of the Tabard Inn, proposes this storytelling contest among the pilgrims as a way to entertain each other during their journey. He asserts that the pilgrim who tells the best tale will be rewarded with a meal at the others' expense upon their return.