Okay so, what the heck, Florida? This has to be the wildest legend yet, and so far, there have been some mouth droppers. Not that I'm complaining. Florida has to be the most colorful and interesting state I've lived in next to my beloved home state of California. But this story is...interesting.
Maybe you've heard of it, but for those who haven't, we're going to have a little chat. A friend of mine on TikTok was the one to point out the story to me (shout out to you, friend). I'd almost forgotten I'd linked my Newsbreak account and all my stories to my TikTok profile.
It can be difficult to see all the comments on TikTok, especially once your video gains traction, which is why I'm surprised I caught this one. Often, my friends will comment on an underperforming video to ensure that I can see their message. And I'm glad she did, because then I'd have missed this story entirely.
"Just waiting for you to do a story on the Headless Horseman of Kissimmee. I've lived here my whole life and trust me, I can tell you some stories."
Of course, the only proper reply was to answer, "message me," and thus started my descent into what is easily my favorite Florida ghost story so far. What can I say? Since I was a girl and saw the Disney adaptation of the famous novel: "Legends of Sleepy Hollow" I was both horrified and intrigued by the idea of a demonic headless horseman riding through the night with a flaming Jack-o-lantern and black, feral horse coming to collect your head.
And now, apparently, you don't have to head to DisneyWorld during Mickey's Not So Scary Halloween Party to visit him. You just have to head to Kissimmee.
If you have not been to Kissimmee, it is a truly charming slice of Florida just outside of Orlando. I filmed out at the waterside a few weeks back, and it was so tranquil. Families enjoying walks in the park, a birthday party on the grass, couples enjoying a quiet sit by the water. To me, Kissimmee seems like the least sinister place you could go in Florida, including Disney World, but something I've learned living here a little over a year is that Florida is never what you expect or see on the surface.
According to my friend, and a very popular legend that is available on multiple reputable sites via a simple Google search of "Headless Horseman Kissimmee" brought up the same story my friend told me: That the spirit of a Headless Horseman has been seen by "hundreds" of people by a tree called "Dead Man's Oak"
And of course, the story of the Dead Man's Oak is perfectly terrifying and fitting for a backstory about a Headless Horseman. Local Kissimmee legend states that by the ancient Dead Man's Oak, "hundreds" have witnessed "the apparition of a headless horseman riding a white horse" dating back as far as a century ago. Sadly, the horseman is said to potentially be the "spirit of a man who was captured by Spanish soldiers and beheaded beneath Dead Man’s Oak." However, the latest sighting was way back in 2000.
I don't know about you, but I think it's time for a road trip out to Dead Man's Oak. My only question is: Who's coming with me?
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