Seven people—the Hegemony Consul, Colonel Fedmahn Kassad, the poet Martin Silenus, the scholar Sol Weintraub, the detective Brawne Lamia, and the tree Templar Het Masteen—have been chosen to go on the Shrike pilgrimage to the Time Tombs (strange monuments that are traveling backward through time) on the planet Hyperion.
Uh, we're not sure what's going on or why, and we don't know if they know either. On top of all this, the Time Tombs are guarded by the Shrike, a metallic, four-armed, red-eyed creature that controls time and kills at will. Fabulous! Where do we sign up for this trip?
The pilgrims are all basically strangers to one another, forced to live and travel together for weeks on their journey. According to Meina Gladstone, Hegemony CEO, there's a traitor among them, a spy for the Ousters, sworn enemies of the Hegemony. This journey isn't going to be short and easy; it's a pilgrimage, after all. To pass the time, and perhaps avoid certain death, the pilgrims decide to tell their stories around the campfire while eating s'mores.
Okay, so there aren't any s'mores, but there is plenty of food, and the stories are really interesting. How are they all connected to Hyperion, the Shrike, and to each other?
On the Templar treeship Yggdrasil (that a good name for a treeship), which is taking the pilgrims to Hyperion, they listen to Father Lenar Hoyt's story, The Priest's Tale. After, they land in Keats, the capital city of Hyperion, which if you hadn't guessed, draws a lot of its culture from the life and poetry of the poet John Keats. From there, they take the barge Benares upstream while listening to Colonel Kassad's Soldier's Tale and Martin Silenus's Poet's Tale. At the end of the barge's voyage, they reach the edge of the Sea of Grass, a huge plain of—you guessed it—grass.
What you probably didn't guess is that's it's razor-sharp and infested with serpents.
Thankfully there's another method of transportation waiting: a windwagon. The pilgrims board the automated vehicle and sail across the Sea of Grass. On the windwagon, they listen to Sol Weintraub's story: the Scholar's Tale. That night, war comes to Hyperion. They watch helplessly as the Ousters shoot down Yggdrasil. After seeing his beloved craft destroyed, Het Masteen disappears. The next morning they discover that his room is empty... except for the vast quantities of blood splattered all over the walls. Gross.
Despite the missing Templar (and the possibility that there's a murderer in their midst), the pilgrims continue their journey across the mountains. On the tramcar between the highest mountains on the planet, Brawne Lamia shares her Detective's Tale.
Finally, they reach Chronos Keep, a castle built by Shrike's worshipers. It's deserted. And finally, the Consul not only shares his tale, but also reveals that he's the Ouster spy. After a brief debate, the pilgrims for some reason decide not to execute him for treason. Looking out the window, they see Het Masteen walking down the mountain toward their destination: the Time Tombs.
The remaining six pilgrims link arms and skip into the valley of the Time Tombs singing a song from The Wizard of Oz. (No, we're not joking.) It looks like Hyperion is just the beginning of the story.