Why cant the headless horseman cross a bridge?

Answer 1

The Headless Horseman can't cross a bridge because of a local legend that states he can only be defeated or banished by crossing a bridge. This belief stems from the idea that the bridge serves as a boundary between the realms of the living and the dead, and crossing it would symbolize his defeat. Additionally, the bridge represents a place of safety for the residents of Sleepy Hollow, where they feel protected from his supernatural presence.