There’s a local legend that has been passed-down for generations in Osceola County, one that has found its way into a few ghost books, albeit with very little information, about the Dead Man’s Oak. After receiving a few emails about this haunted tree, I decided to investigate this legend and see if there was anything to it. I figured if there was such a tree I could get a picture of it.
The first version to this legend alleges that some Spaniards captured a man on a white horse in the vicinity of the Dead Man’s Oak. The man was strung up by his captors and beheaded beneath the tree for having committed a crime against the Spanish. Allegedly, a headless horseman on a white horse can still be seen at midnight roaming around this old oak tree. In some accounts the headless phantom has been accused of chasing people. The problem with this story is that this was hostile Indian territory during the Spanish period. It seems highly unlikely that any European, including Spaniards, or even criminals on the run, would have been foolish enough to venture into these parts. The second version has a man being hanged from the oak for cattle rustling and it is his ghost that has been scaring folks. Although in this case the phantom retains his head.
Depending on the source, Dead Man’s Oak is located about 18 miles south of Kissimmee, or about ten miles south of St. Cloud, or two miles north of Canoe Creek, or somewhere on the road to Kenansville. The directions were not easy to follow and to make matters worse; there are a couple of roads to Kenansville and thousands of oaks.
I tried to ask for directions, but I found most people were new to the area and not in tune with local history, although a few had heard about the Dead Man’s Oak legend. After a morning of driving and backtracking, and having little success, I figured it was time to ask a local native. I was in the middle of cow country when I saw a rancher leaning against a pickup loaded with hay bales. I pulled over and asked, “Have you ever heard of a tree called the Dead Man’s Oak?” I was surprised when he came back with, “You mean that hanging tree back up the road, where they say the ghost rider is?” He directed me back up the road to a lone oak tree standing in a pasture, about fifty-feet from the road.
I took a photo of it, but it didn’t look weird enough to me, and certainly not old enough to have such a ghostly past. It appeared to be no more than 75 years old. I was later directed to several other oaks, all masquerading as the Dead Man’s Oak. My conclusion is that nobody really knows the location of the Dead Man’s Oak, or maybe it no longer exists, perhaps it never did exist, except in a persistent folk legend that still haunts imaginations.