Ichabod Crane finds himself 250 years in the future and realizes that evil accompanied him to modern-day Sleepy Hollow; Ichabod forms a bond with Detective Abbie Mills after the Headless Horseman murders the sheriff.

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 the Horseman. Meanwhile, an encounter from Crane's past weighs heavily on him, and details about his first encounter with Katrina are revealed.