Mr. Great Heart escorts Christiana, her children, and Mercy to the Porter’s Lodge and returns to his Lord because they had not requested for him to guide them completely through the journey; nonetheless, they meet the family and lodge for the night. In the morning, the family asks them to stay longer, which they agree to and remain there about a month, and while there, Prudence reviews the catechism with the boys and finds that they are well equipped with the Truth; also Matthew becomes sick because of the fruit that he ate from Beelzebub’s Orchard, but he is made well with medicine from the Physician; and when it is time for them to continue on their journey, Mr. Great Heart returns to guide them the rest of the way.
Piety walks with the Pilgrims for a short while in the Valley of Humiliation and makes known to Christiana where the place is that Christian fought with Apollyon and explains that those occasions are the fruit of a pilgrim's actions and should expect battles. Next they come to the Shadow of Death, but it was easy-going due to their Guide and daylight; also Great Heart had to fight a Giant, and he again is victorious and praises God.
Now the Pilgrims and their Guide meet Old Honesty, an old Pilgrim, and when he learns that Christiana is the wife of Christian, he is overjoyed and turns to the boys and gives them words of wisdom. Then Great Heart and Old Honesty discuss Mr. Fearing who was a Pilgrim, fearful of nothing but his final acceptance, and next Mr. Selfwill who uses Scripture out of context to justify his choices.
Because Christiana is weary, Mr. Honest directs them to an Inn, and because Gaius the Innkeeper is a good disciple, they decide to stay over a month; however, this first night over supper, they discuss several points: Christian’s ancestors, such as Stephen, James, Paul, Peter, Ignatius, Romanus, and Polycarp, all who have suffered harm and death for their love of a Pilgrim’s life; that Matthew, Christiana’s eldest, should marry Mercy; and how women are highly esteemed in the Faith, and that by what they do demonstrates that they are sharers in the Grace of Life. Later it is decided that they will go to the cave of Giant Slay Good as revenge for all the pilgrims he has obstructed in the Way, and when they do, they find that he has captured Mr. Feeblemind; therefore, they kill the giant and bring Mr. Feeblemind, a sickly man, back to the Inn with them.