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It appears that Brom Bones was aware of what transpired on the night of the Harvest Ball because he defeated him in a duel and Izabod was able to escape him.
Actually, Brom is Ichabod's sole chance of escaping the Hessian Rider while he is being followed. But as soon as Ichabod crosses the bridge to imagined safety and is nonetheless beheaded by the Horseman, who "pass by like a whirlwind," it becomes clear that Brom was mistaken about the bridge's protecting abilities.
Ichabod is always reading spooky tales, sharing them with others, and hearing other people's accounts.
Just then Ichabod's saddle gave way, and Gunpowder started racing for the bridge. Ichabod managed to ride bareback across the bridge, but the Headless Horseman threw his "head" at him and knocked him off the horse.
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