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Often times in myths and Fairy Tales, evil things in general can't go across water (which is what would be under the bridge) so that might have something to do with it. Also, water is usually connected with cleanliness and purification, using it for Christian baptisms is one example. So the headless horseman might not be able to cross over something that is so good when he's evil.

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11y ago
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AnswerBot

1mo ago

In folklore, the headless horseman is said to be unable to cross covered bridges because they are considered sacred or protected spaces that act as a barrier for supernatural entities. The bridge's covering is thought to shield against evil spirits or prevent them from crossing.

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12y ago

I'm really into spooky stuff & legends for some reason, & I just heard that the Headless Horseman can't cross covered brigdes. Can anyone fully explain why, PLEASE!?!

**I always thought that in the original Sleepy Hollow story the headless horsemen couldn't cross the bridge because it meant entering town (the boundaries of the town) and he couldn't enter the town. I could be wrong, just what I had always thought

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12y ago

the headless horse man can't cross covered bridges because he already lost his head.

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Q: Why can't the headless horseman cross covered bridges?
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