Cow Pen Creek

The old train trestle over Cow Pen Creek where the “Headless Horseman” is said to haunt can still be seen from the nearby road.

With Halloween approaching this weekend, children all over the Wiregrass will no doubt be filled with as much haunted ghost stories as candy, and Coffee County has its share of those legends including its own “Headless Horseman.”

Legends of a “Headless Horseman” are almost as old as the country itself with seemingly dozens of stories all across the country with the most notable being the “Legend of Sleepy Hollow.” Coffee County has its own “Headless Horsemen,” however. In fact, part of what is now known as Freedom Drive in Enterprise was once called “Headless Horseman Road” based on the legend.

The legend was documented in multiple issues of the Pea River Historical Society’s Pea River Trails newsletter. According to Pea River Trails, there are two legends that surround this story.

The first version of the tale says that a young man decades ago was hung under the train trestle – that can still just barely be seen from the road that crosses Cow Pen Creek outside of Enterprise near Level Plains. The legend goes that anyone that dared to climb the old trestle would see the image of a ghostly man without a head.

Another version of the legend – and possibly the most popular version of it with locals – claims that a daughter of a Confederate soldier fell in love with a Union soldier during the Civil War. The young couple planned to run away together and get married, but her father found this out and rounded up a group of Rebels to capture the Yankee soldier. According to the legend, the young soldier fled and was captured by the Rebels near the old trestle and during the chase his horse fell over the train tracks causing the young man to fall on the tracks themselves. There, a train zoomed by and beheaded the young Union soldier. According to this version of the legend, that soldier returns on occasion – under the moon – searching for his head.

Legends surrounding the tale also claim that young people traveling to the location of the old trestle in hopes of seeing the horseman have had their cars stalled before the horseman made his appearance. In fact, another legend claims that a man chopping firewood nearby was approached by the horseman carrying his own head. This scared the young man so badly that he eventually fell to his death and some claim that the sounds of his screams can be heard when the horseman approaches.

“Be quiet and still, and count,” the legend says of those that venture near the old trestle looking to see the horseman. “As you do, look far down (the train) tracks and watch for a bright light, until you see the light and a floating figure of a man without a head.”

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