- "Open your eyes, sir! Yes, you, basket face. I thought only horses slept standing up!"
- —Ichabod Crane, enraged at a baseball game
When Ichabod Crane goes missing, his wife, Katrina, appears to Lt. Abbie Mills in a vision warning her that the Headless Horseman will return to Sleepy Hollow by nightfall. A frantic Abbie seeks help from the mysterious Henry Parrish, who holds vital clues about how Crane can vanquish his dangerous blood tie to Headless. Meanwhile, an encounter from Crane's past weighs heavily on him, and details about his first encounter with Katrina are revealed.
Ichabod and Abbie bond over a baseball game, with both parties shouting at the umpire. After the game, Ichabod remarks that he feels like he is at home, and Abbie tells him that he is. The two go their separate ways and Ichabod visits the cemetery, visiting the grave of his late wife Katrina. Suddenly, an unknown party shoots a tranquilizer dart into Ichabod's neck and puts a bag over his head as he begins to black out.
Abbie is pulled into a vision with the Headless Horseman pursuing her through an abandoned house. She finally enters a room with witches casting a spell, and is confronted by Katrina. Katrina informs her that someone has abducted Ichabod, and that by finding "The Sin Eater", Ichabod can be sanctified of his sins, which will separate him from the Horseman. Abbie snaps out of the vision and barely escapes hitting an oncoming tanker truck. Abbie tells Irving of Ichabod's abduction, and Katrina's vision about the Sin Eater. Irving approaches it with skepticism.
Meanwhile, Ichabod awakens to find himself in a room with several men in possession of a book, supposedly an accounting of Ichabod's life. They want to verify that Ichabod is real and isn't a demon in disguise. They have Ichabod retell a story from his past about Arthur Bernard, a recently freed slave who was interrogated by the Redcoats.
Abbie, with help from Jenny, locates Henry Perish, the Sin Eater, who stopped helping to free people of their sins years ago, and requests his help in freeing Ichabod from his blood tie to the Horseman of Death, but he refuses. However, he does tell them where they can find him, as he has been captured.
Once confirmation of his identity is verified, the Free Masons inform Ichabod that the only way for the Horseman of Death for good is for he himself to die.
Abbie locates him just in time to try and stop him from drinking a poison that would kill him, but is unable to stop him once he's convinced that it must be done to stop the Horseman.
Henry Parish arrives, after having a change of heart, and begins to help Ichabod to sever his blood tie to the Horseman. Eventually, with the aid of the soul of Arthur Benard, Ichabod is freed of his blood tie to Death, his sin absolved.
At the end, Death arrives to the cave where Ichabod was buried alive and it is assumed that he is aware that Ichabod was buried here and has become freed of his connection to him.
- In Japan, this episode is known as The Freemason and his Sin [フリーメイソンと罪 Furīmeison to Tsumi].