This seemingly ordinary two-lane road in Kentucky is home to several chilling legends.

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Bluegrass Legends

The Bluegrass State is no stranger to legends and ghostly lore.  There is a multitude of haunted sites in Kentucky, and countless local legends.   From being home to the infamous Waverly Hills Sanatorium to a notoriously haunted bourbon distillery, Kentucky is full of tales of paranormal hauntings. One haunting legend will take you on twists and turns down an unassuming two-lane road, with an eerie name.

Haunted Sleepy Hollow Road

When you hear the name Sleepy Hollow, you are instantly transported to the famous short story The Legend of Sleepy Hollow by Washington Irving.  The book follows the story of Ichabod Crane and the headless horseman who haunts the town of Sleepy Hollow.  While the Sleepy Hollow Road in Kentucky may not have its own headless horseman, it does have its fair share of eerie legends surrounding it.  Are you brave enough to drive this eerie road at night?

The Legend of the Ghostly Hearse

One of the most common local legends that surround Sleepy Hollow Road is the legend of the ghostly hearse.  There are a few different iterations of this tale, but most have the same story at their core, ghostly headlights follow you and eventually, you realize it is a hearse.  The hearse is said to attempt to run you off the road.

Wave3 interviewed Rod Whitenack of Louisville Halloween who explained the legend as follows:

"Basically someone is driving down the road. Lights behind them and they say 'someone's following me,'" said Whitenack. "It makes them have to go faster and faster. Then the car pulls out in front them and they find out it's a hearse that's been following them."

This tale often ends with the car being followed running off the road down a drop over 30 feet in some places. Cry Baby Bridge is another stop on this long stretch of road.

There are many other eerie legends surrounding Sleepy Hollow Road in Kentucky, Kentucky Monthly has an in-depth piece breaking down many of these legends, and so does Wave3.  After learning about Sleepy Hollow Road, are you brave enough to drive along this windy rural road at night?