The Legend of Sleepy Hollow

What happens when Ichabod tries to get across the bridge?

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approaches the bridge that crosses the haunted stream, and his horse comes to a sudden halt. Ichabod sees a large, dark figure on the edge of the brook. 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.

The figure goes into motion—he is a large horseman on a large black horse. The horseman rides along beside Ichabod and Gunpowder without saying anything or making any sign. Ichabod, bothered by this, tries to outpace him, but the horseman quickens his steed as well. Ichabod tries to lag behind, but the horseman keeps pace with him no matter what he does.

Ichabod tries to sing again, but his mouth is too dry with fright. He is not quite sure what it is, but something about his companion is greatly disturbing. 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. Ichabod panics and attempts to get away by suddenly dashing forward. 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.

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. They approach the bridge by the church at which (in the stories that Ichabod has heard) the Headless Horseman vanishes. 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. It hits Ichabod right in his head and knocks him off of his horse.

Source(s)

http://www.gradesaver.com/the-legend-of-sleepy-hollow/study-guide/summary-paragraph-57-to-postscript