Haunting Stories of Sleepy Hollow Road

Sleepy Hollow, and in turn, Sleepy Hollow Road, have long been the subject of creepy tales surrounding tragic events big and small. The town became well-known after a novel by Washington Irving of the same name, which was later adapted to the movie screens depicting the tale of the Headless Horseman. While that may be the stuff of legends, the town has other ghostly mysteries are rooted in actual events that have transpired over the decades and centuries past. These mysteries are often connected to locations and edifices where brutal, sometimes horrendous events have taken place. However, it is not just the old buildings that are haunted even the road that leads into the small town has ghostly apparitions welcoming visitors/residents with a fright.

Sleepy Hollow Road has ghostly tales of its own that are sure to scare everyone, even those with the toughest nerves of steel. It is a long and winding road going up a steep hill surrounded by thick wooden trees. The area it traverses through was thought to be cursed by Native American tribes back in the day and abundant tales of unexplainable phenomena today confirm the earlier beliefs.

The School Bus Children

One of the most prevalent haunted stories of Sleepy Hollow Road is that of the school bus children who died on the road when their bus overturned. Some say the haunted children come from a school that used to be located along the road in the 1930s. The teacher or camp counselor at the school killed those children. Still, others say that the school had burnt down leading to the death of those children whose ghosts can be seen walking along the side of the road wearing their uniforms from the 1930s. The ghosts of these children appear only momentarily before disappearing.

Mary, the Lady in White

Also sometimes known as the White Witch makes frequent appearances on Sleepy Hollow Road terrifying drivers. There are different narratives on who the Lady in White is and whether she was a witch. However, she is known to haunt the road where it meets Mt. Misery Road. That is where the White Witch appears in front of drivers scaring them to death as their cars pass through her ghostly figure. Some people say the White Lady is the ghost of a woman named Mary who died on this road after being pushed out of the car by her boyfriend. In other versions of the same story, it is said that she jumped out of the moving car and died as a result of her injuries. Still, others say that she was a teenager who was hit by a car on her way home.

No one really knows the real identity of the woman in white. Some say she was a patient at a hospital that used to be located near the road back in the 1840s and 50s before it was mysteriously burned down as people were trapped inside the building. It was re-built again at the same place years later before being burnt down a second time. Local folks believe the Lady in White was either a nurse or a patient at that hospital who torched the place herself. People also claim to see burning specters as they pass by the place where the hospital used to be accompanied by screams and cries of those who tragically lost their lives in those fires.

Some people say that Mary is the ghost of a woman who was hung on the side of the road during the witch hunts of the 1600s and 1700s. Her soul is eternally trapped wandering this road from the trauma of her death.

The Ghosts of the Overpass

If you cross the Sleepy Hollow Road where the Northern State Parkway overpass is, you might come across the corpses of the teens who killed themselves by hanging from the overpass. Drivers who honk their horns or switch their lights on and off while going through the underpass can sometimes see the spectral images of people hanging from the overpass. Another similar account mentions, two young teenage boys who were killed by a car because they couldn’t see it approaching them. Drivers are advised to honk their horns before entering the overpass lest the ghosts of those teenage boys jump in front of them as they go through.

Some say that a woman who was killed on the road in the seventies sometimes helps push the cars through if they find themselves stuck on the road by the bridge. People report seeing a pair of spectral hands who help push their car when it is stopped under the bridge and put in neutral. There are also reports of the ghost of a little child that appears to be sitting by the roadside by itself. Apparently, that child was killed in a collision near the bridge.

The Ghost of the Policeman

One of the most horrifying and scary experiences that people go through is when they are stopped on the road by a police officer. Upon checking their ID and documentation, as the officer turns around people notice blood on his uniform and that the back of his head seems to be missing. The officer is no real officer at least not in the sense that he is living. He is apparently the ghost of an officer who died on this road in the line of duty from a shotgun blast to the back of his head. No one seems to know when this officer died or what exactly happened to him but the sight of him is enough to scare people and confirm the horrible reality that he experienced in his last moments.

The Hell Dog of Sleepy Hollow

Given the variety of ghostly encounters that people have on Sleepy Hollow Road, it is no surprise that not only humans, but animal spirits also haunt the road scaring passersby half to death. In one of the most frightening brushes with death itself, people describe seeing the ghost of the hell dog from the thick woods that surround the Sleepy Hollow Road. This Hell Dog is unlike any other while eyes glowing bright red from the thick dark trees. Some people say it is an omen of impending death for whoever sees them.

The Ghost Carrying a Basket of Heads

While there might be people walking along the side of the road, drivers are cautioned not to pick people up from the road especially those they see wandering on the road on their own at night. These wanderers may not be actual people but rather ghostly apparitions walking along what feels to them like a familiar haunt. There is one ghost in particular that likes to walk along the road carrying a basket in his hands. This is no breadbasket but rather a basket full of severed heads as people often discover to their horror upon stopping to help the man.

The Ghostly Carriage

The difficulty of driving at night is that it is often hard to see, even with your car lights on. Drivers on Sleepy Hollow Road sometimes report seeing lights behind their car, apparently from another car that seems to be “following them”. The first instinct people have when they discover these lights is to try and go a bit faster to lose these people, whoever they may be so that their journey can continue normally. However, people soon realize that this car is attempting to overtake them, and as it passes by, people realize it is not a car at all! In fact, the lights they were seeing were from a ghostly carriage that had been behind them this whole time. This is a dangerous situation for the drivers to be in because this ghostly carriage is attempting to drive the people in the car down a cliff from a turn up ahead after it passes them. Drivers who are not careful may find themselves at the bottom of the cliff if they survive the fall.

Whether one believes in ghosts or not, it is best to stay cautious when driving, walking, or hiking along Sleepy Hollow Road. Plenty of ghosts and spirits of those who died on the road or in the nearby wooded areas still haunt passersby today.

Sources Cited:

https://www.wave3.com/story/26157561/kentuckianas-monsters-myths-and-legends-sleepy-hollow-road/