The pilgrims pause to celebrate their victory over Maul at the spot where Christian first met Faithful. Traveling onward, they meet an old pilgrim named Old Honest asleep under a tree. Old Honest wakes up scared, mistaking Christiana’s group for thieves. Learning that Christiana is the wife of Christian, he calms down.

Great-heart asks Old Honest if he knew a pilgrim named Fearing, and Old Honest says that Fearing was his former companion. Great-heart explains that he guided Fearing to the gate of the Celestial City and tells of their journey. Fearing boldly faced the challenges that terrify others but feared hell, because he was unsure of his commitment to the Celestial City. Christiana, the boys, and Old Honest discuss how fear is a spur to goodness and the love of God if it is used properly. Old Honest tells of another wayward pilgrim named Self-will, who did whatever he pleased. The pilgrims express their disapproval. After recapping both stories, Old Honest adds that many who consider themselves pilgrims fail in some basic way.

The three robbers who robbed Little-Faith in Part I approach the group. The pilgrims take refuge in the house of Gaius, who says he opens his doors only for pilgrims. Gaius invites them to eat and talks at length about various religious matters. He delivers a long defense of women, arguing that although sin came into being through a woman, so too did salvation when Mary mothered Christ. After the meal, Gaius proposes that they all go out to find a giant named Slay-good that has been ravaging pilgrims lately. The pilgrims find Slay-good in a cave about to devour Feeble-mind, a weak pilgrim. They defeat Slay-good and free Feeble-mind.

During the month spent with Gaius, Christiana’s eldest son, Matthew, marries Mercy, and her youngest son, James, gets engaged to Phebe, Gaius’s daughter. As the time for departure nears, Great-heart invites Feeble-mind to accompany them. Feeble-mind resists, saying he is too ignorant for pilgrimage. Great-heart insists that he is obligated to help the feeble-minded. A handicapped pilgrim named Ready-to-halt also joins them. On the road, Old Honest and Great-heart discuss many characters that Christian met on his pilgrimage, including Faithful and Hopeful.

They lodge at the home of Mnason, who invites them to dine with his various friends, including Contrite. Contrite says that the locals feel a burden of guilt after the unjust execution of Christian’s friend Faithful and have since become more moderate. The pilgrims spend a long time with Mnason. During this time, Mnason’s daughter Grace marries Christiana’s son Samuel, and his daughter Martha marries Christiana son’s Joseph. A fierce dragon with seven heads emerges from the woods and frightens the pilgrims. The dragon menaces the children of the village. Great-heart joins forces with Mnason’s friends to subdue the monster.

The pilgrims climb the hill called Lucre where Demas tempted Christian with silver. They find a man who cares for the children of pilgrims, and Christiana, now a grandmother, tells her four daughters-in-law to hand over their babies to him. The group proceeds onward. Great-heart, Old Honest, and Christiana’s sons decide to slay Giant Despair. After killing him, they spend seven days demolishing his castle. The group rescues the prisoners Despondent and his daughter Much-afraid, who are nearly starved.