Even if you’re not from New York, you’ve probably heard of Sleepy Hollow. The Hudson Valley village gained notoriety from Washington Irving’s short story “The Legend of Sleepy Hollow,” which was first published in 1820. The eerie tale of Ichabod Crane and the Headless Horseman has captivated readers and thrill-seekers for more than two centuries.
Today, Sleepy Hollow is a commuter town of roughly 11,000 people, but it hasn’t shed its ghostly past. The village still leans into its 17th-century roots, and its haunted reputation is woven into local life and tourism. In fact, many people swear that Sleepy Hollow is truly touched by the supernatural.
Here’s why Sleepy Hollow is my favorite haunted place in New York, along with some creepy spots you’ll want to explore if you make the trip this fall.
A Town Steeped in Legend
Washington Irving’s “The Legend of Sleepy Hollow” centers on Ichabod Crane, a superstitious schoolteacher who moves to the quiet village of Sleepy Hollow. One night, he encounters the Headless Horseman, the ghost of a soldier who lost his head during the Revolutionary War. The Horseman rides at night, carrying his severed head and haunting the surrounding woods.
The modern-day village of Sleepy Hollow (once called North Tarrytown, renamed in 1996) has fully embraced the legend. Its signage features the Horseman’s silhouette, and he even serves as the mascot for Sleepy Hollow High School. Local businesses and attractions proudly reference the lore, too. Visitors can peruse The Horseman’s Shop or Horsefeathers, for example.
In autumn, the legend truly comes alive. Residents decorate their homes for Halloween, and the village hosts festivals, cemetery tours, haunted events, and celebrations of Washington Irving’s legacy. Visitors might even spot a costumed Headless Horseman roaming the streets.
The Old Dutch Church
In “The Legend of Sleepy Hollow,” Ichabod Crane flees from the Headless Horseman, heading toward the bridge by the Old Dutch Church. This is an actual building—and one of the oldest churches in New York, opened in 1685. As you can expect, it’s purportedly haunted…