Christian meets up with his former fellow townsman Faithful, who fled the City of Destruction shortly after Christian left. Faithful reports that the townspeople discussed their impending doom, but that few took it seriously enough to leave. Faithful says that Christian’s old acquaintance Pliable returned to town and was mocked for the dirt on his clothing from the Slough of Despond.

Faithful says he himself escaped the Slough but was tempted by a wanton woman and by an old man named Adam the First, who promised Faithful any of his three lusty daughters if he would stay. Faithful reports that he declined the offer, knowing it would be slavery. Even though he rejected Adam, Moses appeared to strike down Faithful in punishment, Christian concludes, for secretly being attracted by Adam’s offer. Faithful reports that shame tried to turn him from his holy path, attacking religion as unmanly. Christian congratulates Faithful on his fortitude and then tells him of his own adventures.

Another townsman named Talkative joins the two. Faithful is initially impressed by Talkative’s devoutness, since Talkative likes discussing religious topics. Christian sees otherwise and takes Faithful aside to tell him that Talkative’s faith is all in words, not in deeds. He knows Talkative from his life before and knows that he has a fine tongue but little else. Rejoining Talkative, Christian asks him to explain the difference between speaking out against sin and abhorring it. Talkative has trouble seeing any difference between the two, and Christian sets him straight. Irked, Talkative leaves them.

Emerging from the wilderness, Evangelist meets Christian and Faithful and congratulates them on overcoming their obstacles. Evangelist says they will soon enter a powerful enemy city where one of them will die. The narrator identifies this city as Vanity, home of a great and ancient festival called Vanity Fair, where tawdry products are traded and Beelzebub is worshipped. At Vanity Fair, Faithful and Christian are mocked, smeared with dirt, and thrown in a cage. Given a chance to repent, they stay true to their righteous hatred of worldly possessions. They are condemned to death for belittling Vanity’s false religion. Faithful tries to speak in his own defense but is burned at the stake and carried off to heaven. Christian is remanded to prison but escapes later.

Christian continues his journey joined by a new ally, Hopeful, and a stranger named By-ends, who sees religion as a way of getting ahead in the world. Christian refuses to let By-ends accompany them unless he affirms that poverty is an aspect of faith. By-ends is turned away and joins other religious fortune hunters, who are stunned when Christian denounces them. Christian and Hopeful enter the plain of Ease, where a gentlemanly figure named Demas entices them with buried silver and dreams of wealth. They spurn him, telling him they will not be nudged from their course by riches. On their way, they notice the pillar that once was Lot’s wife who made the mistake of looking back at what she had left behind on her own path to salvation. Christian and Hopeful vow not to make the same mistake themselves.

Moving onward, they follow a man who says he knows a shortcut to the Celestial City. They realize it is not a shortcut after they fall into a pit. A storm rises, and they nearly drown when the rain floods their hole. When the rains abate, they come out and continue on. They find shelter near the Doubting Castle owned by the Giant Despair, where they sleep. The giant wakes them and says they must be punished for trespassing. His wife, Diffidence, encourages the harshest punishments. They are imprisoned and beaten and contemplate suicide, finally deciding against it as a sin. Christian remembers he has a key called Promise that will open any door in Despair’s castle. Christian and Hopeful escape and mount a sign warning future travelers away from Despair.