The Wailing Bride of Sleepy Hollow
October 26, 2025
There’s a road that hugs the river near Sleepy Hollow — narrow, uneven, lined with trees that lean too close. The kind of road you only take when you’re lost or late. Most people keep their windows up when they drive it at night.
A few years back, a tow truck driver pulled over there after midnight. Flat tire, empty stretch of road. While he was checking his tools, he heard it, a single note rising out of the fog. High and thin at first, then deeper, like wind caught in a throat.
He thought it was an animal. Then he heard the voice inside it.
They say she’s older than the Horseman’s tale. A woman who walked into the Hudson on her wedding night. Some say her fiancé drowned that morning. Others say she found out he never meant to show. Either way, she never made it home.
Locals call her the Bride, but the name doesn’t fit anymore. What’s left of her wears a veil that moves like smoke and a mouth that never stops calling. People hear her from the water, the sound scraping across the current until it reaches the road. It’s always the same: one drawn-out wail, then silence.
Every decade or so, someone disappears.
Once it was a couple who stopped to film the fog. Once a man walking home from the station.
They always find the same thing — the car still running, the driver’s door open, tire tracks ending where the pavement does.
The tow truck was recovered a week later. Keys in the ignition. Lights on. Driver’s boots sitting side by side in the dirt.
Nobody knows what he saw before he stepped out of them.
If you ever find yourself on that road and the fog starts to thicken, don’t listen for her.
Keep your eyes on the center line and your hands on the wheel.
The moment you try to make out what she’s saying, that’s when she knows you’re listening.
Author’s Note
Sleepy Hollow’s lesser-known legends often tie to the Hudson River rather than the Horseman. Stories of a weeping woman near the waterline date back to the 19th century and blend elements of Dutch, Native, and colonial folklore.
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