The Legend Of Kentucky’s Sleepy Hollow

I am trying something new on the blog. I research a read a lot of stories about the paranormal in Kentucky. Some of them have lots of back stories and some of them are just stories and legends that have become part of Kentucky’s haunted history over the decades. These Pit Stop Stories will look at those legends and maybe give you a chill while you are sitting alone in your bedroom at night.

When you hear the word “Sleepy Hollow” you probably think of the Disney cartoon “Icabod and Mr. Toad” from 1949, which was based on “The Legend of Sleep Hollow” by Washington Irving, first published in 1819.

The Adventures of Ichabod and Mr. ToadCourtesy: Walt Disney Productions 1949

Kentucky has its own Sleepy Hollow. Sleepy Hollow Road begins in Jefferson County and crosses into Oldham county near Norton Commons on the northeast side of Louisville.

This two-lane highway runs along the edge of a ravine and is covered by a thick tree canopy that all but blocks out the sunlight. Thankfully, the good people at the Kentucky Transportation Cabinet installed guardrails to keep you from plunging more than 30 feet down to the bottom.

Sleepy Hollow Road has a couple of different ghost stories attached to it. The first is the legend of a black hearse. The legend goes, that as you travel down Sleepy Hollow Road at night, headlights will suddenly appear behind you. The headlights get closer and closer but the vehicle won’t pass you, so you speed up. When you are on Sleepy Hollow Road you are pinned in on either side. jagged rocks on the left and the ravine on the right. You continue to speed up and are whipping around the turns. Then the vehicle starts to pass you. Then you see it. A large black hearse with dark tinted windows. Instead of passing you, the hearse rams you and forces you off the road and down into the ravine. I imagine it looks like the hearse Dracula drove in the 1987 horror movie classic “The Monster Squad”.

Still from “The Moster Squad” – Courtesy: Taft Entertainment Pictures 1987

The second legend has to do with a bridge and a baby, multiple babies actually. I couldn’t find exactly where on Sleepy Hollow Road the covered bridge used to be located, but the website says the bridge called “Cry Baby Bridge” was located over Hite Creek. The legend goes that women would take their unwanted babies and throw them off the bridge and into the creek. Hite Creek drains into Harrods Creek, which drains into the Ohio River. Now, the bridge is gone, but if you are driving down the road late at night, roll down the windows and turn down the radio and you might just hear the children thrown into the river, still crying out for their mothers.

If you want to go check out Sleepy Hollow Road for yourself, it is located off Interstate 71 on Brownsboro Road in Eastern Jefferson County, right past Norton Commons.

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