Is that the wind? The trailing cry of a baby? The wailing of a mournful mother full of regret? These are thoughts that might pass through your mind as you make the winding, tree-lined drive that is Sleepy Hollow Road in Oldham County.
It’s a 2-mile curvy stretch of road that is steeped in so much lore, your heart can’t help but race as you round every turn in full anticipation that you are about to become your very own urban legend.
On nights when Sleepy Hollow Road is not the backdrop of your worst nightmares, it’s just a two-lane country road where high school kids might joyride. Most people who have had encounters in the hollow still speak fondly of youthful memories cruising the stretch. And while everyone I spoke with had his or her own “legend” experience of Sleepy Hollow, no one really seemed too scared to return. Instead, the feelings seem more tragic than terrifying.
That said, when I approached the hollow one night in August, it was after dark, and I was alone. Heat lightning silently lit a canopy of clouds to an ominous purple hue. As I drove toward the hollow, the lights of outstretched urban sprawl faded in my rearview mirror, and total darkness encompassed everything. I began descending into the hollow with nothing to guide me but my headlights. The thick veil of bone-chilling blackness filled the rearview mirror.
The road curves a lot through the hollow. Each curve is a completely blind turn, any one of which taken individually and put on any other road in the world could earn the nickname “Dead Man’s Curve,” especially when you factor in the 30-foot drop-off to the hollow floor. At the bottom—in the lowest, darkest depths of Sleepy Hollow Road—a bridge crosses Harrods Creek, a good-sized tributary of the nearby Ohio River. From the bridge, the road ascends, refreshingly leading you back out of the hollow.
And when you come out of the hollow, you find yourself well removed from the urban sprawl on the other side. You are on a two-lane country back road beneath the famous blue moon of Kentucky and a sky filled with stars, their glow unabated by the light pollution of nearby Louisville. It’s a breath of fresh air compared with the dark through which you’ve just passed.
Let’s start with the broad strokes and most common legends that surround this stretch of road. First, and perhaps the hardest for me to accept, is the infamous hearse that allegedly barrels down on cars from behind and forces them off the road and into the hollow below. While this story is the best-known, it appears to me to be the most far-fetched. Should I believe that not only does a vehicle have a spirit that it can conjure at will, but also that an inanimate object, such as a car, even has will to begin with? In addition, that it would be intelligent enough to have an arbitrary mission, like pointlessly running other cars off the road? It would seem that, if I were to believe a car has a conjure-able spirit, it would be oblivious to its surroundings, and were it to pull up close to cars in the hollow, it most likely would be because the spirit of an inanimate object would be unaware of its surroundings, not because it was purposely trying to hurt anyone. But that’s just me overanalyzing urban mythology, I suppose.
I’m not a skeptic when it comes to the supernatural. However, I need more proof before I can say without a doubt the spirit realm exists. So, I’m not here to preach or try to disprove the mythos of Sleepy Hollow Road. In fact, I kind of love the various stories that have stuck to this relatively short stretch of road.
Perhaps the most chilling—and the one I find most compelling and even the most likely to believe—is also the story I would most hate to believe. And that is about the bridge that crosses Harrods Creek at the bottom of the hollow. The bridge is known as Cry Baby Bridge. Today, it’s an unassuming crossing of concrete and steel, but for many years, an old covered bridge stood there. It was there at Cry Baby Bridge where, according to legend, mothers would throw deformed children—or products of incest or bastards or, if she was a slave, her owner’s child that she had given birth to—into the water below to be washed out to the Ohio.
It’s a horrific image to have in your brain: how desperate a mother would be to feel compelled to toss her own baby from a bridge. Or perhaps it speaks to the time—how poor would the quality of life be for such children that their mother would rather end their lives than subject them to a lifetime of being ostracized and/or enduring servitude.
Many travelers have claimed that if you stop at the bottom (which I would not recommend, since there’s no shoulder to pull over onto) or pass through with your windows down, you can sometimes hear crying babies calling out for their mothers or despondent mothers mourning the loss of their children or even the splash of a cherubic body hitting the cold water beneath the bridge.
There’s a folk song the early settlers of the area brought with them from England that has become inextricably tied to Cry Baby Bridge over the rolling procession of generations called “A Cruel Mother.” It relates the tale of a mother who is preparing to be married but gets pregnant by another man. When her child is born, she kills him immediately and then proceeds to the church for the wedding. The song features such heartbreaking lyrics as: “O, mother dear, when we were thine … Out ye took a little penknife … An ye parted us and our sweet life.”
Other common stories have involved Devil’s Point, a location in the hollow that was the site of alleged satanic rituals during the late 1970s and early ’80s. There also have been multiple sightings of a soldier on horseback up on the ridge. Some have mentioned lights flying beside their car or moving through the trees, while others have even claimed the pass is a time warp, where they may enter the hollow at a certain time and, after what seems like a five-minute trip through the pass, come out on the other side and discover that hours have gone by. However, it seems to me this could be related to kids on joyrides under the influence of mind-altering substances more than any supernatural phenomenon.
Perhaps most interesting to me are the conversations I’ve had with people who are familiar with the hollow. Two people who have never met each other told me eerily similar stories about an old woman in the road. One person went so far as to refer to her as “The Sleepy Hollow Witch” as if she were common knowledge. But outside of these two independent stories, my research uncovered no other reports of such an experience.
In both cases, the incident occurred near Cry Baby Bridge. They described the woman as older and, therefore, it would be doubtful that she was the mother of a lost baby. While the storytellers were traveling from different directions, both were on the same side of the bridge when they rounded a corner and saw the woman standing in the middle of the road. One swerved to miss her and ended up hitting a guardrail, while the other didn’t have time to swerve but drove right through her before she disappeared.
What is one to make of such conjecture? I drove Sleepy Hollow Road with paranormal investigator Teressa McCammon hoping to find out. While she had never personally investigated the hollow (the terrain would make a thorough investigation incredibly difficult and dangerous), McCammon had some interesting thoughts about the countless stories that pepper the rich history of this stretch of road. “This place is very, very dark—you can’t see the sky if you wanted to,” she says. “The turns are dangerous, and you’re descending into what seems like hell. The natural terrain writes its own narrative. I would be more surprised if this road didn’t have stories like these.”
The day McCammon and I and ventured to the area, it was the middle of the afternoon, the sky was bright and blue, the clouds puffy and white, and the sun high and yellow in the sky. And as we approached the hollow, rain began pouring. The sky still blue, the clouds still white, the sun still high. I had to wonder if someone or something knew we were coming to tell a story it didn’t want told.
We wound through the pass and then through the country roads beyond. We strolled through the Harrods Creek Cemetery, which supposedly is where the tailgating hearse is headed and where the ghost of a 6- or 7-year-old girl has been seen entering at night. It’s still active with fresh graves, but there are headstones dating back to the early 19th century, and some with pre-Revolutionary War birth dates.
I had no paranormal experiences in my times through the pass, but of those I spoke with about their Sleepy Hollow experiences, I am the exception. All mentioned they heard or saw something somewhere in the hollow. “Different people are sensitive to those sorts of things,” McCammon says. “A lot of the people that are [sensitive] don’t exactly welcome it, and a lot of people that aren’t are the ones asking all the questions. But it makes sense: If you’re experiencing these things that terrify you, you want nothing to do with it. And if you aren’t, you want to know what everyone is so afraid of.”
Maybe she’s right. Maybe it’s just curiosity in those of us who don’t see it that makes us want to see what everyone else is talking about, and that’s what led me to Sleepy Hollow in the first place.