Before leaving the Inn, Gaius gives his daughter Phebe to James for a wife, and just as they are preparing to leave, Mr. About Tofall comes by the Inn, and it is decided that he should go with the rest of the pilgrims, as he is a suitable companion to Mr. Feeblemind. When they arrive near to Vanity Fair, they stop at the home of Mr. Mnason who invites his friends Mr. Contrite, Mr. Holy Man, Mr. Love Saint, Mr. Darenot Lie, and Mr. Penitent to visit the pilgrims and have fellowship; much is discussed including the two things one must have when on pilgrimage: courage to stay on their path and an unpolluted life so as not to defile the name of a Pilgrim. Over the time that the Pilgrims remain with Mr. Mnason, Christiana’s last two sons are married to Mr. Mnason’s daughters, and Mercy continues working for the Poor, while the men of the group must battle a Monster that “made great havoc of children, and yet was governed by a woman.”
After they leave the home of Mr. Mnason, and pass through Vanity Fair without much concern, they come by the Pillar of Salt toward the Delightful Mountains to the meadow where little ones are raised in the care of a Man “who gently leads those who have young.” Finally, as they arrive at By-path Meadow, near Doubting Castle where Giant Despair resides, Great Heart decides it is his responsibility to overcome evil and declares to destroy the Giant and his castle, as old Honest and Christiana’s four sons agree to go with him; therefore, another victory is won for Great Heart, and they rescue two more Pilgrims, Mr. Despondency and his daughter Much Afraid.
When they arrive at the Delightful Mountains, they meet with the Shepherds who show the Pilgrims new places: such as Mount Marve, where a man moves hills with his Words to teach Pilgrims how to move difficulties out of their path using their Faith; Mount Innocent, where two men, Prejudice and Illwill, throw dirt in vain at Godlyman, dressed in all white, because they hate his goodness though dirt will not stick to him; Mount Charity, where a man makes coats out of a bundle of cloth that never dwindles because if you desire to give in labor, “you shall never lack the ability to give.” Mercy also desires to see the Byway to Hell, in which the Shepherds show her, and she hears the lamenting of those who suffer in that place; and then Mercy asks for the Mirror that shows the face and likeness of the Prince of Pilgrims himself, which they also give to her.