They find hoof prints and the trampled saddle, and they finally find Ichabod’s hat lying next to a smashed pumpkin. When Ichabod has not appeared by dinnertime, either at Hans Van Ripper’s place or the schoolhouse, Hans becomes worried enough to send out a search party. Gunpowder appears at Hans Van Ripper’s gate the next day without saddle or rider. It hits Ichabod right in his head and knocks him off of his horse. As soon as Ichabod gets across the bridge, he looks back to see if the ghost has vanished-but as he does, Ichabod sees the ghost stand up in his stirrups and throw his head at Ichabod. They approach the bridge by the church at which (in the stories that Ichabod has heard) the Headless Horseman vanishes. In Gunpowder’s frenzy, they gain some ground on the Headless Horseman, but Ichabod’s saddle starts to slip and falls off just as he grips Gunpowder’s neck to hold on. The Headless Horseman easily keeps pace, however, and when they reach the road to Sleepy Hollow, the frenzied Gunpowder veers off in the opposite direction, toward the infamous church.
Ichabod panics and attempts to get away by suddenly dashing forward. When the horseman is suddenly in relief against the sky, Ichabod realizes something ever scarier-he is headless, and he has his head resting on his saddle in front of him. He is not quite sure what it is, but something about his companion is greatly disturbing. Ichabod tries to sing again, but his mouth is too dry with fright. Ichabod tries to lag behind, but the horseman keeps pace with him no matter what he does. Ichabod, bothered by this, tries to outpace him, but the horseman quickens his steed as well. The horseman rides along beside Ichabod and Gunpowder without saying anything or making any sign. The figure goes into motion-he is a large horseman on a large black horse. He knows he cannot outrun a ghost or goblin, so he tries to summon his courage and asks, “Who are you?” He tries to get Gunpowder the horse to continue on, and he starts singing a psalm. Ichabod sees a large, dark figure on the edge of the brook. He then approaches the bridge that crosses the haunted stream, and his horse comes to a sudden halt. He makes it past the fearsome Major Andre’s tree, but he has to calm himself by whistling. As he rides, all the ghost stories he has heard come back to him, and he gets more and more uneasy as he approaches the infamous church where the Headless Horseman most often rides. Ichabod wakes his horse and sets off during the darkest and quietest hour of night. The narrator does not know what passes in this conversation, but Ichabod leaves the place looking rather crestfallen, and readers must use their imagination it seems that in one way or another, Katrina was using him to secure his rival’s affections. The party eventually breaks up, and Ichabod stays behind to talk to Katrina.
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