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John finds Vertue walking with difficulty. Vertue insists that he must continue his journey and explains that while Wisdom’s teachings have reinforced his belief in the rules, he also believes that the mortal self is fundamentally opposed to them. To live correctly, one must detach from the world as much as possible. John, however, interprets Wisdom’s lessons to mean that the rules should lead to a better understanding of the world rather than a harsher one. Their differing interpretations lead to an argument. Vertue says he needs to find the harshest place to live as punishment for the crime of existing. Despite John’s attempts to follow and reason with him, Vertue shouts and throws rocks at him.
John follows Vertue, but the valley becomes increasingly treacherous. When he catches up, he finds Vertue struggling to climb a spur of rock that blocks the path. When Vertue reaches the top, he shouts at John and sends a boulder rolling toward him. John dodges it, but Vertue disappears. John decides to return to Wisdom’s Valley, but a Man climbs down from the rock and tells John to keep following Vertue, insisting that they will recover if they stay together. When John says that he can’t climb the rock, the Man offers to help him. Once he reaches the top, John realizes that the Man has vanished, leaving him alone again.
John finds himself stuck on a narrow ledge above the canyon floor with cliffs above him. Feeling abandoned, he tries to find strength in the idea that his eternal spirit, which should not care about the mortal body’s fate, is driving him along. However, he struggles to fully connect with this idea and cries out for help. He realizes that he is praying, something he equates with the Landlord’s rules. John tries to reassure himself that it is just a metaphor.
John feels comforted by this idea of metaphors and finds the strength to continue along the cliff. The difficulty increases as he goes, requiring constant mental effort. He recognizes that he is praying but reassures himself that this connection to a greater part of himself is not to be confused with the mythical Landlord. He starts to sing and acknowledges the limitations of humanity and the idea that everyone is an idolater in prayer unless divine grace changes their metaphors into communication.
In John’s dream, a Man appears, offering him bread and water. Before leaving, the Man says that John should not treat the help he received as metaphorical. If the divine can answer his pleas, it can also issue commands. John admits his reluctance to commit to the rules.
John wakes to the horror of the canyon’s edge again. Feeling trapped by the landscape, he panics as he realizes that he can never be alone, free, or entirely in control again. As he walks, he sings about his longing for the freedom of the past. The return of the Landlord overshadows the Island, and he realizes that he can no longer seek it freely but must follow the Landlord’s plans. He consoles himself with the idea that the real Landlord might differ from what others say about him.
John hears a bell and finds a small chapel in a cave. Inside is a hermit named History, who invites John to rest. John confides in the hermit about his quest for the Island. History listens and then says that he once traveled the lands and describes them as having strange and destructive customs. They arose from ignorance, as the inhabitants were wealthy but disconnected from the world. They misunderstood or rejected simple, good things due to their isolation. John then asks about the Island, but before History can answer, it starts to rain, pausing their conversation.
After listening to the rain, John resumes the conversation. History says that the visions of the Island come from the Landlord, who provides not only the rules but also pictures for those who cannot read. The pictures lead people to Mother Kirk, the guide to the Landlord. History notes that the struggle between the rules and the pictures is ongoing, with the Enemy spreading illiteracy and confusion. Yet the Landlord continually sends new messages. They then talk about the Shepherd People, whom John insists are Pagans. History clarifies that the Shepherds were different because they could read and were given the rules. History also says that the Shepherds and Pagans were incomplete and needed the Landlord’s Son. Finally, he advises John to reconcile with Vertue.
History explains that the Landlord’s messages, which take many forms, universally create a longing for something beyond the world. John also learns that the Romantic pictures, which arose in the land of Mr. Enlightenment, depicted the actual landscape and awakened a longing that transcended idolatry. The Enemy countered by belittling the Romantics, confusing their desire with ordinary pleasures, making their profound longing seem trivial. History explains that rejecting old messages does not prepare one for new revelations. True understanding comes from recognizing the continuity of the Landlord’s messages over time. John realizes that those who ridiculed old messages never became recipients of new ones, as this only aided the Enemy.
John tells History that he is afraid that the Landlord’s plans for him might be different from his desires. History reassures John, explaining that while it might be different from his current understanding, the inability of earthly things to satisfy him is evidence of a deeper, divine source for these desires. As night falls, he lights a lamp and provides John with food and shelter. Despite John’s admission that his visions of the Island have grown rarer, History compares them to the natural progression of human love. As John falls asleep, History sings about longing for divine intervention to keep watch over him and fulfill desires that he can no longer feel himself.
John wakes in the cave to see a bright light. It comes from Contemplation, who stands between him and the sleeping History. She tells John to follow her and explains that the version of Contemplation he knew was merely a shadow of her true self. As she leads him from the cave, they travel in an orb of light across the chasm, over mountains and the sea, and arrive at an ocean of light and dewy fields that John recognizes as the Landlord’s castle. As they approach a set of high walls, a terrified John tries to escape, but Contemplation continues to lead him toward the gates. He screams and awakens from the dream.
John decides to leave despite the dangerously narrow ledge outside, as he prefers the thunderstorm to the fear of the Landlord’s castle. As he goes, he is tormented by visions of falling into darkness and his uncle George’s face. Amidst the storm, a voice commands him to turn back. It is revealed to belong to Reason, who is ready to fight. John turns back.
John sees a face that vanishes into the clouds but knows it’s still watching him. The face says that his fear of the black hole represents the fear of surrender and helplessness. The face declares that the Landlord’s Son feared these things as well and that John must either submit to it or be forced. John decides to surrender willingly and is told that by doing so, he reclaims his liberty. The face says that he should go to Mother Kirk. As the moonlight returns, John sees figures and water far below in the chasm. He begins his descent down the cliff and finds it surprisingly easy.
John arrives at the bottom, where a crowned Mother Kirk stands by a pool, surrounded by silent onlookers. Vertue, already naked, waits nearby. John announces his surrender to Mother Kirk, who instructs him to strip off his clothes and dive into the pool. Despite his fears, John undresses, pulling off some of his skin along with his clothes. As he approaches the pool’s edge, ghostly figures of people such as Enlightenment, Media Halfways, Sigismund, Sensible, Humanist, and Broad try to stop him with various arguments. However, Vertue encourages him not to hesitate and jumps into the pool. John shuts his eyes and follows.
John travels through the dark pool and catacombs within the mountains. He encounters Wisdom, who claims that John’s adventures are mythological, not factual. Another voice reassures John that while it may be mythology, it is divine mythology meant to reveal the face of God through the imagination. John emerges in a forest, and he and Vertue join a group of pilgrims who have undergone similar trials. Reason accompanies them. As they journey west along a river, they eventually reach the white beaches of a bay at the world’s end. John sees the Island, and the longing he feels is transformed by the presence of his thousands of companions. The sight of the Island brings humility and a mix of fear and hope.
John and Vertue are approached by a guide named Slikisteinsauga, whose sight enhances the vision of those who travel with him. Slikisteinsauga reveals that the Island is the same as the Eastern Mountains they saw from Puritania. John feels disheartened, thinking his efforts have been wasted because he could have achieved his goal without the journey. The guide reassures him that the Landlord directed their path, making it the correct journey despite its roundabout nature. Vertue reflects that their earlier trials seemed like crossing the brook, and the guide explains that they will encounter this metaphorical brook repeatedly, each time believing it to be the final challenge, until they ultimately overcome it for good. Slikisteinsauga prompts them to begin their journey back east, cautioning them that the landscape will seem different.
Slikisteinsauga leads John and Vertue back across the canyon. They arrive where the main road meets Mother Kirk's chair. However, the landscape has changed dramatically: The northern side has crags, ice, and black clouds, while the southern side has swamps and jungle also fading into black clouds. Despite the changes, John knows it’s the same place. Slikisteinsauga explains that the land they see is the actual reality of their journey. Beyond the northern crags lies the Arctic Sea and the Enemy’s country, connected by the Isthmus Sadisticus, where a cold, constrictive dragon resides. John is tasked with dealing with this dragon, while the southern swamps lead to the Southern Sea and the Isthmus Mazochisticus, home to a hot, corruptive dragon that Vertue must confront. As they set off, Vertue begins their journey with a song reflecting on the nature of good and evil, the struggle between divine love and infernal desire, and the choices humans face.
Vertue looks for any sign of Mr. Sensible’s house but finds none. Slikisteinsauga explains that their eyes now only see realities, so Mr. Sensible is now invisible, as he borrowed appearances from others, taking these traits without truly understanding them. Slikisteinsauga explains that the true source of his teachings was a great Steward who emphasized love as the foundation of all commandments.
As John travels east, he sees an island of willow trees in the swamp. Slikisteinsauga explains that this place, previously called the Valley of Wisdom, is now Limbo. The inhabitants are men like old Mr. Wisdom, who have the soul’s desire but refuse to fulfill it due to pride, sloth, or timidity. These men live forever in desire without hope. When John questions the fairness of their suffering, Slikisteinsauga explains that desire without hope is a choice they make and that the Landlord preserves this desire. The guide emphasizes that the pain of wanting is better than not wanting at all and that the Landlord’s love and wrath are one.
When John questions if there is a black hole, which Slikisteinsauga confirms, he expresses disbelief that the Landlord would allow such a place to exist. The guide explains that the Enemy frequently accuses the Landlord of cruelty, but the Landlord’s kindness is evident in the freedom he grants his tenants, even though this freedom allows them to make poor choices. The Landlord cannot force someone to choose differently if they have made it impossible for themselves to do so. The black hole, the guide also clarifies, is not created by the Landlord but is a container for the evil caused by the tenants’ choices. Slikisteinsauga then sings about the delicate balance between choices and consequences and the importance of vigilance in making decisions.
As John, Vertue, and Slikisteinsauga continue their journey, they meet a grotesque, skeletal figure named Superbia, one of the Enemy’s daughters. Superbia, who had previously appeared to John as the three pale men in the hut, obsessively polishes a rock clean of any life. She sings, boasting of her self-sufficiency, purity, and rejection of the flesh. Her extreme self-sufficiency momentarily sways Vertue. Slikisteinsauga warns Vertue not to confuse repentance with disgust and cautions against using one vice to fight another. Vertue sings about the struggle with pride and understanding the true nature of the self and the divine as they move on.
John, Vertue, and Slikisteinsauga pass Ignorantia and discuss whether the ignorance of the Clevers will ever be cured. The guide explains that it is unlikely, as the northern people have abandoned even the basic knowledge that once connected them to enlightenment—a shift driven by the rebellion of the lower classes and the consequent focus on machinery by the sub-tenants. Vertue expresses hope that this revolution might have a positive side, but Slikisteinsauga laughs, explaining that these changes are an illusion and that the promises of machinery are false. He predicts that the iron cities will eventually crumble and that nature will reclaim the land.
The trio stumble across a disturbing scene: a concourse of disfigured men with vermin growing from them. Among them is a witch, Luxuria, who tempts them with a cup, promising temporary relief from suffering. John witnesses a young man struggling against temptation, only to succumb and sink into the swamp. As they travel, the witch attempts to tempt John, exploiting his weariness and despair. He combats her by creating verses that help him focus. Eventually, the witch leaves, but John feels more tired than ever.
As John and Vertue prepare for their final challenges, Slikisteinsauga tells them that they are now between the two land bridges where the cold and hot dragons reside. Vertue heads south to face the hot dragon, while John goes north to confront the cold dragon. John begins his climb up the rocky terrain and enters a dense mist, where he hears the dragon singing about its loneliness and regret. John is filled with disgust, pity, and a desire to negotiate with the creature. However, his body instinctively prepares for battle. When the dragon encircles him, John waits until it tightens its loop before making a decisive jab with his sword. The dragon’s breath freezes John, giving him strength and clarity. He kills the dragon and stands victorious.
John returns to Slikisteinsauga, whistling a tune. Soon they hear a cry from the south, and Vertue returns ablaze, warning them to keep their distance. He recounts the dragon’s fight, describing how it breathed fire on his shield and sword, setting them on fire. Vertue tells them that he ultimately killed the dragon despite the heat and ripped out its heart. He celebrates his victory with exuberant singing.
As John, Vertue, and Slikisteinsauga continue their journey, their spirits are high. Vertue loses his usual dignity, and John is tireless. They meet an old fiddler who plays tunes that cause them to dance instead of walk. John stops and cries as they arrive at a ruined cottage by a river—his father’s house in Puritania, now abandoned, as his parents have passed beyond the brook. Slikisteinsauga reassures him that he will cross the brook himself before nightfall. As they approach the Eastern Mountains, Vertue laments that whatever lies beyond the brook will not be the same and that something is ending. John counters Vertue’s melancholy with a more hopeful perspective, arguing that humans’ connections are meaningful. They reach the brook and cross over.
In the last section of the novel, Lewis draws a clear distinction between John and Vertue in order to emphasize the completion of John’s character arc. John and Vertue both respond in very different ways to the lessons they learned in Wisdom’s house. John adopts an optimistic view, while Vertue takes a pessimistic one. He references a biblical passage (Isaiah 64:6), declaring the mortal self a flaw in the perfect goodness of the Spirit, and subjects himself to self-punishment, including breaking off his friendship with John and self-isolating. John’s encounter with “the Man,” whom Lewis positions as representative of Christ, shifts his previously pantheistic perspective to a theistic one, leading to the book’s first song, which is titled in other sources as “Footnote to All Prayers.” The Man later returns to give John bread and water, reminiscent of the Christian sacrament of communion, and advises him that if God can help, he can also command: “If it can answer when you call, then it can speak without your asking. If you can go to it, it can come to you” (168). When John wakes again, he creates another song, “Caught,” during which he acknowledges that his fears have come true and that he must relinquish his quest for the Island in favor of acceptance of the Landlord.
Lewis frames the Man’s guidance as instrumental in directing John toward History, suggesting a connection between historical engagement and The Search for Spiritual Truth. When John meets with History in his cave, the hermit says, “If the feet have been put right, the hands and the head will come right sooner or later” (179), referencing the biblical scripture found in John 13. History also explains how morality (the rules), mythology, and the pictures complement each other and the ways in which both are utilized by the Landlord, alluding to The Role of Reason and Imagination in Faith. In Lewis’s allegory, the Landlord’s Son (Christ) reconciles the non-Jewish “Pagans” and the Jewish “Shepherds” consistent with the biblical account of Jesus. History also elaborates on the ways in which the Landlord’s message has evolved, from medieval courtly love culminating in Dante’s Divine Comedy to the Romantics’ love of nature in the 19th century. Lewis suggests that each message, though imperfect, reminds one of their journey. When John falls asleep, he hears History’s song, “The Naked Seed,” alluding to a new beginning.
After overcoming his fear of the black hole and, therefore, of death, John descends into the canyon and reaches the floor of Peccatum Adae. While he feels defeated, he is also finally ready to follow Mother Kirk’s guidance—suggesting a willingness to embrace the Christian community of faith. In addition to John’s symbolic baptism, John’s dive into the river provides another connection to Lewis’s actual lived experience. In 1930, he finally learned to dive. His description of the event mirrors John’s own lack of grace, as it “[i]s not a good dive, but, at least, he reache[s] the water headfirst” (199). At the water’s edge, eight wraiths appear in an attempt to stop him, each representing people he met on his travels—alluding to the inherent differences between the philosophical and cultural ideologies that Lewis critiques and Christian doctrine. Once John is in the underground passages, the voice of God finally speaks to him, saying, “For this end I made your senses and for this end your imagination, that you might see My face and live” (200), evoking biblical language and reinforcing The Role of Reason and Imagination in Faith.
When John re-emerges from the water, it is to a world filled with light and color, symbolic of a religious conversion experience. His guide, an angel named Slikisteinsauga, summarizes John’s journey and explains that the Landlord had brought to him the shortest route to his destination, evoking the biblical passage of Genesis 50:19-20, in which God uses evil for good. John’s and Vertue’s respective victories over the two dragons demonstrate their respective moral and spiritual growth over the course of the story. Lewis completes his narrative by returning John to the place his journey began and the brook he once feared, signifying both the end of his journey and the acceptance of death. As they cross the brook and Lewis’s dream ends, he hears the three of them singing. John and Vertue sing about their joy and gratitude, which contrasts with the angel's lament for not knowing loss or sorrow.
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