The Pilgrim’s Regress is a 1933 allegorical novel by C. S. Lewis that was heavily inspired by John Bunyan’s The Pilgrim’s Progress (1678). The book chronicles the journey of a man named John to find the elusive Island he glimpses in a vision. He encounters various characters representing different worldviews and schools of thought along the way. These encounters critique contemporary intellectual trends and spiritual movements, reflecting Lewis’s views on the inadequacies and pitfalls of modern philosophy and secularism. Ultimately, John’s quest leads him to realize that true fulfillment comes from embracing the Christian path, positioning the story as symbolic of Lewis’s own path to Christianity.

This guide refers to the 2014 e-book edition published by Harper Collins.

Content Warning: The source text and this guide contain references to racism and suicide.

Plot Summary

The Pilgrim’s Regress is told from the perspective of an omniscient narrator, who describes John’s journey as a dream. The book is split into 10 named books.

Book 1, “The Data,” describes John’s early life in Puritania, where he is subjected to strict rules set by the mysterious Landlord. John’s curiosity leads him to explore a nearby wood, where he glimpses a beautiful Island that he longs to see again. As he grows older, John has a sexual encounter with a mysterious girl in the woods but soon becomes disillusioned. Overwhelmed by the weight of the Landlord’s rules, John revisits the woods. He sees another vision of the Island and decides to leave home to find it.

In Book 2, “Thrill,” John travels westward. He meets Mr. Rationalism, who convinces him that the Landlord does not exist. He also meets Mr. Vertue and Media Halfways. Media leads John to her father, Mr. Halfways, who tries to convince John that the Island he seeks is a state of the soul. He plays a song on his harp that gives John a vision of the Island, but the experience is fleeting and unsatisfying. John and Media share a brief romance interrupted by Media’s brother, Gus, who dismisses Media and their father’s beliefs. The following day, Gus takes John to Eschropolis, a steel city that represents modern ideals.

In Book 3, “Through Darkest Zeitgeistheim,” after John escapes from Eschropolis, he enters a pass belonging to a giant called the Spirit of the Age. He is imprisoned in a dungeon, suffering under the giant’s gaze and the jailor’s torment. Despite the jailor’s attempts to demoralize him, John defies the logic presented to him. Eventually, an armored woman named Reason arrives and challenges the giant with three riddles. Unable to answer them, Reason destroys him, allowing John to escape his imprisonment.

Book 4, “Back to the Road,” shows John’s brief journey with Reason. As they travel, she explains the meanings of her riddles and how they reveal the Spirit of the Age’s hypocrisy, causing John to laugh and his remaining chains to fall off. Eventually, tired by her pace, John decides to part ways with Reason. She directs him to the main road and advises him to go left. However, he goes right to resume his quest.

In Book 5, “The Grand Canyon,” John reunites with Vertue at the edge of the Grand Canyon, which blocks their progress. They meet a woman named Mother Kirk, who offers to carry them across, but they refuse and decide to find another route. Seeking shelter, they stay at Mr. Sensible’s house. After a night of discussions about philosophy and good living, they decide to leave, and Mr. Sensible’s servant, Drudge, goes with them. Mr. Sensible is disgruntled but resigned, and they part ways amicably.

Book 6, “Northward Along the Canyon,” shows John, Vertue, and Drudge’s attempts to find a way across the Grand Canyon. They meet three men who offer them shelter: Mr. Neo-Angular, Mr. Neo-Classical, and Mr. Humanist. While Vertue and Drudge scout the northern route, John stays behind to talk about philosophy with the three men. Vertue returns exhausted and reports that there is no way across. He also warns them of a man named Savage, who plans to attack them with the dwarfs he rules over. Despite Vertue’s warnings, Mr. Neo-Angular, Mr. Neo-Classical, and Mr. Humanist remain skeptical.

In Book 7, “Fool’s Paradise,” John and Vertue leave the trio and head south. John loses sight of Vertue, and when he finds him again, Vertue cannot see or speak. John leads him down into Wisdom’s Valley. There, Mr. Wisdom gives them advice about their quest and the nature of their desires. He explains that the Island, the Roads, and the Rules are all real in some sense, but not in a literal manner. During their stay, John observes the curious behavior of Wisdom’s children, who seem unaware of the nocturnal escapades they perform. John also dreams of a woman named Contemplation, who shows him another vision of the Island. Vertue recovers but becomes hostile. He flees, and John chases after him.

In Book 8, “At Bay,” John follows Vertue but loses him after the latter climbs a rocky crag. A mysterious Man appears and helps John climb, pushing him to rely on a higher power. At the top, he disappears, leaving John to navigate the rocky ledges of the chasm alone. John finds temporary shelter with a hermit named History. Through their conversations, John comes to terms with the idea that his ultimate longing and the fulfillment of his desires may not be what he initially envisioned.

In Book 9, “Across the Canyon,” John dreams of being led by Contemplation across the chasm and the sea beyond, where he sees the Landlord’s castle. He wakes up terrified and decides to turn back. However, he is confronted by Reason, who compels him to continue. He also encounters a terrifying face that urges him to submit willingly. When he does, he is led to the bottom of the chasm to meet Mother Kirk. Vertue is also there, and she instructs them to dive into a pool and pass through an underwater tunnel beyond. John dives despite fears and temptations from his past trying to sway him. He and Vertue navigate the catacombs and ascend. There, they join with other pilgrims and journey west. Slikisteinsauga tells them that they must return east and cross the brook but warns them that their journey has come full circle. Places they have already visited will look different on the return.

Book 10, “The Regress,” shows the story’s conclusion as John and Vertue, guided by Slikisteinsauga, encounter various allegorical figures and confront the challenges posed by the cold and hot dragons. Vertue battles the hot dragon and emerges victorious but burning, while John successfully defeats the cold dragon. Their journey continues with moments of joy, dancing, and singing but becomes somber upon their return to John’s childhood home in Puritania, which is now abandoned. The story ends with John finally crossing the brook as well.