The book chronicles the tale of two teenage boys and their adventure in the mysterious and dangerous Shadowland where reality and illusions are intertwined.

Straub recalls that the book had its origins in fairy tales he told his son: "Nightly, stories poured out of me, as from an inexhaustible source.

I had no idea where they were going when I started them, but along the way they always turned into real stories, with beginnings, middles, and ends, complete with hesitations, digressions, puzzles, and climaxes.

Another influence was John Fowles's The Magus, "which suggested a way to unite the powerful strangeness resulting from the oral tradition with more conventional narrative satisfactions.

Steve and Tom both have vivid nightmares of a strange figure watching them and of a vulture hovering over them, which seem to oddly connect to Del’s childhood.

At an away football game, Skeleton steals an expensive artifact from the other school, leading to the Carson students to be subjected to extensive and intense interrogation by the principal.

Del discovers the artifact and destroys it, but doesn’t reveal Skeleton stole it to the staff, and the situation is mostly forgotten.

As Collins performs trickery on the boys, warping their sense of time and space, he recounts his past as a World War I soldier and nurse and how he acquired his magical persona.

Also in Shadowland are the Wandering Boys, a group of burly men who acted as Collins’ bodyguards during the War, and Rose Armstrong, a mysterious fifteen year old who stays on the lake.

Believing he had become the man he m murdered, Collins suffered from multiple personality disorder, and ran away from the war to perform in magic shows around Europe.

Collins decides to start his final performance early, crucifying Tom in the main stage and letting the Wandering Boys mercilessly beat Del.

They are joined by Rose, a reincarnation of Rosa Forte, who admits that Collins manipulated her as well as she believed leading them back would save them.

In the present, after interviewing others that Tom Flanagan knew, the narrator meets an older Skeleton at a monastery who seems to have no recollection of the events of the story.

The epigraph for Part Two comes from Roger Sale's Fairy Tales and After: "We are back at the foot of the great narrative tree, where stories can go...anywhere.

Straub’s Shadowland twists itself into its own guts, burrowing deeper into its own dark workings, full of carnage, blood, pain, fairy tales, and occasional flashes of joy and wonder.