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Episode 50…Where is the Dead Man’s Oak?

They call it the Legend of the Dead Man’s Oak, but the biggest mystery might just where the damned and haunted tree may be.

Christopher Balzano and Natalie Crist get into one of the more well-known haunted urban legends of Central Florida, the Dead Man’s Oak. Said to be the site of a headless horseman and his ghostly stead, no one can quit agree on where the tree is located or why the man is trapped on the earth.

After getting into some of the different versions of the story and potential location of the tree, the Trippers dig deeper into the meaning of headless ghosts, including a look at the Dullahan and Crom Cruach.

We’ve started a more in depth look into the Swamp Witch story of Hog Island and some of the lore in the surrounding counties, especially Sumter and Hernando County. If you have any information on odd legends there, let us know at

Here’s the episode, There’s More Than a Swamp Witch on Hog Island to get a feeling for what we’re talking about:

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Episode 48…There’s More Than a Swamp Witch on Hog Island


You can contact us with questions, comments, and your favorite legend or tidbit of folklore at

We’re still knee deep in the #hauntedlove project, so we’re especially looking for ghost stories with a love twist.

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