Upstate NY Town’s Folklore: A Top Spooky Destination in the US

It's the scariest time of the year and just two hours south of the Capital Region is home to one of the spookiest towns in America. It's also one of the scariest stories ever told in American history.

This Ghost Story is Set In One of the Spookiest Towns in America

It is a tale passed down through generations and its central character is The Headless Horseman. The town is in Westchester County, about one hundred and thirty miles from Albany and it is the Legend of Sleepy Hollow.

Where is Sleepy Hollow?

Sleepy Hollow is a small town of about ten thousand people located in Westchester County along the Hudson River.

Sleepy Hollow is the setting for an iconic tale written by legendary historian and writer Washington Irving. He is actually buried in the Sleepy Hollow Cemetery which is a stop along the town's Halloween Tour.

Photo by Chris Boese on Unsplash

The central character in Washington Irving's tale, the Headless Horseman, is said to haunt the town of Sleepy Hollow. He was a soldier and was decapitated during the Battle of White Plains by an American cannonball.

His fellow soldiers carried his body away and left his head on the battlefield. Each night, as the story goes, he searches high and low for his head on horseback with a Jack o'Lantern in hand.

The story takes place in 1776 in Sleepy Hollow and is about a school teacher named Ichabod Crane who comes to the small town of Connecticut. He finds himself at odds with a local man named Abraham "Brom Bones" Van Brunt over a woman named Katrina. After a party one night, Ichabod sees the Headless Horseman and then he is never seen again. If you are inclined, you can head to Sleepy Hollow on Halloween to catch a glimpse.