Proceeding from Gaius' Inn to the outskirts of Vanity Fair, the Pilgrim party halts there to consider the best way of passing through the town where Christian and Faithful had been given such a rough time — Faithful, after a trial before Lord Hate-good, having been mercilessly beaten and then burned at the stake. Saying that he knows a place where they might perhaps find lodgings, at the house of "one Mr. Mnason, a Cyprusian [a native of the island of Cyprus], . . . an old disciple," Great-heart leads them there. As it is dark, they are not seen as they enter the town and make their way to Mnason's house, where they are welcomed.
Old Honest asks his host if there are any good people in town. A few, Mnason replies. How might one meet them, Honest then inquires, "for the sight of good men to them that are going on pilgrimage is like to the appearing of the moon and the stars to them that are sailing upon the seas." Mnason stamps his foot, his daughter Grace appears, and she is dispatched to invite some of his friends to come over for the evening — Mr. Contrite, Mr. Holy-man, Mr. Love-saint, Mr. Dare-not-lie, and Mr. Penitent. In course of the conversation the Pilgrims learn that the people of the town are now more moderate than they were, having been much impressed by the fortitude Christian and Faithful displayed in their trials here. Indeed, since the scourging and burning of Faithful, "they have been ashamed to burn any more." Good people can now walk the streets unafraid.
The Pilgrims stay in Vanity Fair for some time, getting acquainted with the good people in the town, doing them many services. Great-heart here does battle with a monster "like unto no one beast upon the earth," having a body "like a dragon, and . . . seven heads and ten horns." As this monster is carrying off children from the town and wreaking great havoc generally, he has to be disposed of. With some townsmen, Great-heart goes after the beast not once, but many times, and though he does not succeed in slaying him and taking off his seven heads as a trophy, he makes him lame and so severely cuts him up that it seems certain the monster will soon die of his wounds.
During the long stay at the Fair, there is romance and joyous celebration of more marriages. Mnason gives daughters to the two unmarried sons among Christian's "children" — Grace to Samuel, Martha to Joseph. It is noted that all of the brides, Mercy, Phoebe, and the two recent ones, are "very fruitful, so that Christian's name, as was said before, was like to live in world."
Taking to the road again, the Pilgrim company comes to the River of God, or the River of the Water of Life, its banks lined with fine trees and meadows that remain green the year round. Here, by the riverside, are sheepfolds and a house, kept by Compassion and "built for the nourishing and bringing up of those lambs, the babes of those women that go on pilgrimage." Christiana admonishes her four daughters-in-law to commit their "little ones" to the care of Compassion, "so that, by these waters, they might be housed, harbored, succoured, and nourished, and that none of them might be lacking in time to come."
Going on, the party reaches By-path Meadow, into which Christian and Hopeful had erred and been captured by Giant Despair, almost losing their lives in his Doubting Castle dungeon. After some discussion, it is decided that an attempt should be made to slay Giant Despair, tear down his castle, and rescue any Pilgrims in his dungeon. Advancing with Old Honest and Christiana's four sons, Great-heart knocks on the castle gate with a terrific banging. Who is making all that racket? the giant wants to know. "It is I, Great-heart, one of the King of the Celestial Country's conductors of Pilgrims to their place . . . open thy gates for my entrance. Prepare thyself also to fight."
The giant, having conquered angels, has no fears. Smiling at the vain effrontery of the challengers at the gate, he puts on his armor and comes out, a steel cap on his head, a breastplate of fire, wearing iron shoes, and grasping a huge club in his hand. The six men go at him from all sides. When the giant's wife Diffidence comes to his aid, Old Honest cuts her down with one stroke. With all fighting for their lives, Giant Despair is finally knocked to the ground and though he struggles hard, having "as many lives as a cat," is dispatched by Great-heart, who cuts off his head to add to his trophies.
The Pilgrim party then proceeds to tear down Doubting Castle, which takes a week. In the dungeon, filled with dead men's bones, they find and rescue two Pilgrims, Mr. Despondency and his daughter Much-afraid, whom they take back with them to the Holy Way, together with the head of the giant, which is posted on a pole by the lane as a warning not to molest Pilgrims.
At sight of the bloody head, Feeble-mind and Ready-to-halt become "jocund and merry," and music is called for. It now appears, though not mentioned before, that Christiana has been carrying along a viol, and Mercy a lute. They strike up a tune, which inspires in Ready-to-halt a desire to dance. Taking Miss Much-afraid by the hand, he performs sprightfully, even though on crutches, and so the Pilgrims go merrily on their way toward the Celestial Mountains.
In picturing the people of Vanity Fair as being more moderate than they had been at the time of Christian's visit, Bunyan was alluding to the fact that prosecutions and persecutions of Nonconformists had slackened since the passage in 1672 of the Declaration of Indulgence, to which Bunyan owed his release from his first imprisonment, which had stretched out for twelve years. Such prosecutions and persecutions would begin again and become increasingly sharp until James II, an avowed Papist, was dethroned in the Glorious Revolution of 1688, the year of Bunyan's death.
The scene at the house of the Pilgrims' host, Mr. Mnason, is a pleasant one. During the Pilgrims' stay there of a month or more, Great-heart continues his hunt for giants and fiends in general. In the woods outside Vanity Fair, there lurks a "monster" which sallies forth now and again to slaughter people in the town. This monster, a dragon with seven heads and ten horns, is another symbol of the Roman Church. Great-heart moves against him but cannot slay him, being disappointed in not succeeding as he had with the giant Maul, also a symbol of the Roman Church. But Great-heart succeeds in laming the monster, and "it is verily believed by some that this beast will die of his wound." Here, again, Bunyan was indulging in some wishful thinking.
The women, children, and cripples in Christiana's party rejoice with song and dance when the Christian warriors, led by Great-heart, return in triumph from their assault on Doubting Castle, bringing back the head of Giant Despair, after having killed him and demolished his castle. They set the head on a pole beside the King's highway. So that no reader will miss the moral here, Bunyan places a marble slab by the pole, inscribed thus in very lame verse:
This is the head of him, whose name only
In former times did Pilgrims terrify.
His castle's down, and Diffidence his wife
Brave Master Great-heart has bereft of life . . .
This head also, when doubting cripples dance,
Doth show from fears they have deliverance.