John is a young man raised in Puritania under rigid religious rules. After glimpsing a beautiful Island in a vision, he becomes restless and leaves his home to find it. His journey leads him westward across unfamiliar lands where he meets various philosophers, guides, and adversaries. Driven by an intense yearning for the Island, he frequently questions the teachings he encounters.

Mr. Vertue is a traveler who joins John on his quest. He follows a strict, ascetic moral code and insists on adhering to rules even when it causes him discomfort. His punitive approach to life often puts him at odds with the more questioning John, as he relies heavily on extreme self-discipline to maintain his sense of worth.

The Landlord is the mysterious and powerful ruler of the land. He issues complex rules that his tenants must follow, creating fear and confusion for young John. While he rarely appears in person, his influence hangs over the entire countryside, acting as the central authority figure driving the laws of Puritania and beyond.

Mother Kirk is an older woman who wears tattered clothes and possesses deep knowledge of the land's history. She waits near the edge of the Grand Canyon to help travelers cross safely. She offers guidance and safe passage, though her methods require complete submission from those she helps.

Reason is a tall, armored woman wielding a sword who challenges ignorance and false logic. She arrives in the dungeon of the Spirit of the Age and uses riddles to defeat him. She briefly travels with John, offering him clear answers and helping him break free from mental captivity.

The Spirit of the Age is a massive stone giant who imprisons travelers in his dungeon. When he opens his eyes, his gaze turns everything transparent, exposing the grotesque insides of his prisoners and stripping them of their humanity. He relies on psychological torment and reductionist logic to break his captives' spirits.

Mr. Wisdom is an older mentor who provides shelter and philosophical instruction to travelers. He lives in a comfortable valley with his many children. He teaches John about the nature of his desires and the reality of the Island, offering a stabilizing intellectual perspective on the journey.

Media is a young woman who captures John's attention early in his travels. She brings him to her family's home and briefly convinces him that romantic love is the true path to the Island. She is dramatic and emotional, serving as an early distraction from his actual destination.

Mr. Halfways is a solemn, traditional man who plays the harp and entertains guests. He tells John that the Island is merely a state of the soul and uses his music to produce fleeting visions of it. He represents an aesthetic and romanticized approach to longing.

Gus is Media's brother, a cynical young man who mocks his father's traditional art and his sister's emotional outbursts. He values machinery and speed, driving a mechanical bus that he uses to take John away from Thrill. He introduces John to the avant-garde city of Eschropolis.

Mr. Enlightenment is a confident traveler who claims the Landlord is a myth created to control people. He uses flawed scientific reasoning to dismiss John's upbringing and beliefs. He represents a purely rational, secular view of the world that temporarily influences John.

Sigismund is a guard working for the Spirit of the Age who captures John. He dismisses his father's ideas as ignorant and forces John to confront the stone giant. He views all human desires and visions as mere psychological illusions meant to mask baser instincts.

Mr. Sensible is an intellectual host who prides himself on moderation and comfort. He borrows his food, wine, and philosophical quotes from various neighbors and historical figures. He advises John and Vertue to enjoy transient pleasures rather than pursue dangerous, idealistic quests.

Drudge is a hardworking servant who maintains Mr. Sensible's household and barren garden. Tired of his master's pretensions and the constant danger of landslides near the property, he considers leaving his position to join John and Vertue on their journey north.

Mr. Neo-Angular is one of three pale brothers living in a bleak northern landscape. He adheres rigidly to a sense of duty, sharing his food out of obligation rather than kindness. He strongly opposes the emotionalism of the Halfways family and views the world in strict, theological terms.

Mr. Humanist is another of the pale brothers. He maintains a completely barren, minimalist garden that consists of shallow dirt over rock. He claims to be a pioneer of new cultural styles but refuses to do any actual digging or cultivation, preferring the illusion of gardening to the work itself.

Mr. Neo-Classical is the third of the pale brothers living in the north. Like his siblings, he holds strict, reactionary views against modern society, though he tends to dismiss threats like the warrior Savage as mere illusions rather than confronting them.

History is an old hermit who invites John to rest in his cave. He shares stories about the origins of the land's customs and the different ways the Landlord has communicated with people over time. He helps John understand the continuity of these messages and contextualizes the desires John has felt.

Contemplation is one of Mr. Wisdom's daughters. She appears to John in dreams and visions, showing him glimpses of the Island and helping him see beyond his immediate physical surroundings to understand larger spiritual realities.

Slikisteinsauga is a guide whose presence enhances the vision of the pilgrims traveling with him. He explains the nature of their journey, pointing out the necessary choices and paths they must take to complete their quest across the dangerous terrain.

The Steward is an authority figure in Puritania who enforces the Landlord's rules. He hands John a card covered in strict prohibitions and threatens him with severe punishments for disobedience, creating a lasting atmosphere of fear during John's childhood.

Mr. Broad is a Steward who lives comfortably in a sunlit area south of the main road. He is friendly and enjoys theological discussions, but his answers to John's direct questions about crossing the canyon remain vague and noncommittal.

George is John's uncle. His sudden eviction by the Landlord's orders shocks the family and introduces John to the harsh reality of the Landlord's absolute power over the tenants.