Led by Great-Heart, the pilgrims begin their journey down the Hill Difficulty into the Valley of Humiliation. Piety, a damsel from the Porter’s Lodge who has accompanied them this far, tells Christiana that this is where Christian fought Apollyon.

James, the youngest son, finds a pillar on which is written an account and a warning of Christian’s fight. Great-Heart tells the pilgrims that the Valley of Humiliation may be a place where much spiritual fruit is grown, and many pilgrims wish to stop there.

They hear a shepherd boy singing and stop to listen to it, refreshed by the song’s encouragement. Great-Heart says that Christ had his country house in this valley. 

Samuel, the second oldest son, wants to see the place where his father battled Apollyon. Great-Heart leads them there, and they see some signs of the battle still remaining. There is a monument to Christian’s victory there as well. Each spot along the way is some monument to the pilgrim’s struggle and victory as a way to encourage other travelers.

Leaving the Valley of Humiliation, the pilgrim band arrives at the border of the Valley of the Shadow of Death. As they enter, they hear groaning and lamentation and feel the ground shaking.

James becomes sick with fear, so his mother gives him some of the spirits and pills that the physician at the Porter’s Lodge gave her; the boy soon begins to feel better. They see an ugly shape coming toward them. Great-Heart tells the pilgrims to gather close to him, and then the fiend vanishes.

The next troublesome encounter is with a lion. Great-Heart approaches it, ready to do battle. When the lion keeps coming toward them, the conductor leads his party on away from the beast rather than risk a confrontation.

They next pass a pit full of darkness. Christiana tells Mercy that now she sees what her poor husband went through. Great-Heart urges them to be faithful, and Samuel says that these difficulties will make their new home in the Celestial City all the sweeter. Great-Heart guides them past a ditch into which many of the heedless fall.

The pilgrims pass a cave, one which Christian had passed by without incident, but now they see a Giant, Maul, coming toward them. Great-Heart faces him with his sword drawn. He defeats the giant and cuts of its head.

The pilgrims erect a pillar, place the giant’s head on it, and write a sign on the pillar praising Great-Heart’s opposition to the enemy.