Adam journeys to Winchester with Daun Williams. At first he is almost euphoric with hope and good feeling, but by the second day he feels considerably more apprehensive at what he will find in the big city. When they get to Winchester, Daun Williams goes "straight to the largest inn on Cheap Street", but there is room only for the older man. Daun Williams tells Adam to go to the Strangers' Hall, where the monks of St. Swithin's lodge poor pilgrims.
Adam does as he is told, and indeed finds a place to stay among the pilgrims. He searches for Roger, but does not find him; one man advises him to search for his father at the inns, while another red-bearded fellow tells him that "Giles's Hill is where you'll find the minstrels. Adam falls asleep to the sound of the pilgrims talking about King Edward, whom they love, and Parliament, which they scorn.
In the morning, Adam sets out for Giles's Fair. There he finds tremendous crowds, booths and tents of all sorts, and entertainers of every kind. Sadly, "there (are) hundreds of people, there (are) thousands of people, but no Roger". Adam begins to fear he will never find his father and his dog. He seeks out the Street of Dover and is reunited with Daun Williams in his booth. Daun Williams tells Adam that "it may take...several days" to find Roger and Nick, and offers to let Adam spend the nights in his booth.
Adam continues his search during the following days to no avail. One evening, while he is eating dinner, he gets into a conversation with a palmer, who has made pilgrimages to many shrines. The palmer tells him that at the shrine of St. James he experienced a miracle; his lame leg was cured. This gives Adam an idea - he will go to St. Swithin's and pray for a miracle. Joining the other pilgrims at the Cathedral, Adam kneels at the shrine, closes his eyes, and prays "as he had been taught at St. Alban's". He waits for the saint to answer his prayers, but when he opens his eyes, there is still no Roger (Chapter 15).