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This isn’t the old headless horseman tale we all know and love. There’s actually a road that begins in Jefferson County and crosses into Oldam county near Louisville Kentucky. It’s a two lane highway covered with a canopy of thick trees with a hill to its side with more than a 30 foot drop.
The legend is that as you travel down Sleepy Holler Road at night, a set of headlights will slowly appear in your rearview mirror out of nowhere. The headlights will get closer, and closer. If you slow down, the vehicle never passes you. If you speed up it keeps up with you, but will suddenly start to pass you on the huge turns. That’s when you see the car, it’s a large black hearse with all blacked out windows. If you’re lucky it goes on ahead, but for most folks it rams you off the road and down into the ravine below.
The second legend with this road involves a bridge and multiple babies. The bridge was called the cry baby bridge. The legends goes that women would take their unwanted babies and toss them off the side of the bridge there. The bridge is supposedly gone now, but it’s said if you drive down this road at night with your windows down and radio off you might hear babies crying out for their mothers.
Source: https://hauntedkentuckyroadtrip.com/2022/09/06/pit-stop-the-legend-of-kentuckys-sleepy-hollow/
