All of the lands that are outside of the Wicket Gate and the area encompassed by the "walls and borders of that region, wherein lay the way to the heavenly country" are known as the "Valley of Destruction."

This crutch stanches the bleeding and strengthens Tender-Conscience, who must bear with the arrows of Beelzebub until he reaches the House of the Interpreter.

The Interpreter removes the arrows of Beelzebub from Tender-Conscience's body and lodges him for the night, showing him the same emblems and scenes enjoyed by Christian, Christiana, and their children and companions.

Working his way up the hill, he is taken into two caves tended by Good-resolution and Contemplation where he is shown alabaster statues of famous pilgrims from the Bible who had gone on before, and an image of the Celestial City from a carved diamond.

He is given respite and food by Good-Resolution, who warns him about places he should avoid staying while on the hill, and then he continues on the path, where he is stopped by a flattering man Spiritual-Pride, who convinces him there is a quicker way to his award, and leads him to a tower of Lofty-Thoughts with the plans of throwing Tender-Conscience off it, and dashing upon the bottom of the hill below.

Tender remembers the warnings from Good-resolution, and he runs away, going on further he is stopped by an old man, Carnal-Security, who also convinces him to turn from the road, and he leads to a grand palace tended by the old man's wife Intemperance and his daughters Wantonness and Forgetfulness, where he is enticed to drink wine, dabbles with Wantonness and fall asleep in Forgetfulness' arms.

Servants carry him inside and put him on a bed, and music begins to play with the intent of keeping him asleep until he dies, in which case his corpse would be carried down the hill to the path of Destruction, tossed into the fiery Lake of Destruction at the end of the road and die the 'second death'.

He narrowly avoids her grasp to escape, and run back to the main highway on the hill, and reaches the House Beautiful and is let in due to his pass.

At the palace, Tender has long conversations with the virgins Discretion, Charity, Prudence, and Piety about how he escaped danger on the way up the hill, and then is taken to a feast, where he was served by others of the society (Temperance, Decency, Frugality and Bounty).

He then has a conversation on how they came to that place themselves to take on their positions (they were devotees to the woman Religion who originally lived there, and promised to keep her rules), and the discussion of the role of healthy food and moderation in a Christian lifestyle.

He reaches a bridge, and is met with men in rowboats he thought might be murderers and robbers who infested the place.