Christian and Hopeful reach the Delectable Mountains on the outskirts of the Celestial City. They bathe and eat in the gardens and orchards that they discover in the foothills of the mountains, which belong to the Lord Emmanuel. They meet some kind shepherds who welcome them and say that the lord gave them the charge of offering protection to good pilgrims. The shepherds invite them to sleep.

The next morning the shepherds warn Christian and Hopeful of the nearby hills called Error and Caution, which lead some travelers to disaster. The remains of pilgrims, who have made false assumptions about the nature of resurrection, litter the ground beneath Error. Similarly, on the hill of Caution, blind travelers wander among tombs and get stuck there. Both these views show Christian and Hopeful what to avoid. They ask how the blind pilgrims came to wander among the tombs. The shepherds inform them that they tried to take a shortcut to the Mountains, which led instead to the Doubting Castle, where Giant Despair imprisoned them, put out their eyes, and left them to wander on the grounds of his estate.

The shepherds allow Christian and Hopeful to look through a telescope at the Celestial City. Christian and Hopeful tremble with so much excitement that they can hardly see through the glass. The shepherds bid them farewell, give them directions to the Delectable Mountains, and warn them not to sleep on the Enchanted Ground and to beware of someone named Flatterer. The narrator wakes up from his dream.

The narrator resumes his dream and sees Christian and Hopeful go on into the Delectable Mountains toward the Celestial City. They meet Ignorance, a lively lad who accompanies them for a while. Ignorance goes through life hoping for the best. He believes a good life is enough to enter heaven and tells Christian and Hopeful that their path to the Celestial City is unnecessarily long and difficult. He knows of an easier route. Christian tells Hopeful in a whisper that he considers Ignorance a fool. They outpace Ignorance and leave him when they turn into a dark alley full of devils.

In the alley they see a man bound with his face turned away. Christian recalls him as an old acquaintance named Little-Faith and tells Hopeful his story. Little-Faith was traveling with his birthright, a precious jewel, as well as some money. Set upon by thieves, Little-Faith loses most of his cash and is forced to beg for the remainder of his journey, which he complains about ceaselessly. He still has his jewel in his possession but hardly thinks of it. Hopeful asks why Little-Faith did not pawn his jewel for travel money. Christian reproaches him for foolishness, explaining that no believer can sell his faith for material comfort.

Christian and Hopeful follow Flatterer, a deceitful man in a white robe who speaks beautifully but ensnares them in a net. A Shining One arrives and cuts them loose. They meet Atheist, who laughs at their intention to reach the Celestial City. Atheist claims not to have found the Celestial City in twenty years of searching. The pilgrims affirm they have seen it.