The pilgrims now approach the town of Vanity, where Christian met Faithful at Vanity Fair. They lodge with Mr. Mnason, a disciple who is amazed that they have come so far from Gaius’s home.

Learning that Christiana is the wife of the famous pilgrim Christian, Mr. Mnason invites several of the residents of Vanity to meet his guests. They are joined by Mr. Mnason’s daughter Grace.

One of the men from Vanity, Mr. Contrite, tells the pilgrims that the people of Vanity Fair are much more moderate than they were when they murdered Faithful. Mr. Honest and Mr. Great-Heart tell Mr. Contrite of their journey.

The pilgrims stay with Mr. Mnason for a long time during which Grace is married to Samuel, Christiana’s third son, and Mr. Mnason’s other daughter, Martha, is married to the youngest, Joseph. They become acquainted with the people of the town, and soon children are born to the sons of Christian and their wives.

News comes of a Monster coming out of the woods who kills people and kidnaps children but is controlled by a woman. This Monster has the body of a dragon, seven heads, and ten horns.

Mr. Great-Heart leads some of the men to fight the Monster and manages to drive him off. It is believed by many of the people of the town that the beast died of its wounds.

The pilgrims soon continue on their journey, coming to the place where Faithful lost his life. At the River they come across a shepherd to whom Christiana urges her daughters-in-law to give the care of their babies born to them at Vanity.

As the group approaches the Castle Doubtful where lives the Giant Despair, Mr. Great-Heart and the others discuss a plan to destroy the giant and his wife, thus freeing any prisoners inside.

Leaving the women behind with Mr. Feeble-Minded and Mr. Ready-to-halt, the men attack the castle. They kill the giant’s wife, Diffidence, and eventually overcome Despair, cutting off his head to take back with them. They find two prisoners in the castle: Mr. Despondency and his daughter Much-afraid.

They all return to the pilgrims who stayed behind and rejoice at the downfall of the giant. Much-afraid dances with Mr. Ready-to-halt, although the father is too weak from near starvation. Christiana gives him some of her Spirits, which revives him. Mr. Great-Heart puts the head of the Giant Despair on a pole by the wayside to be a warning to fellow travelers.