On the first Saturday in October, thousands of visitors descend upon the spooky hamlet of Sleepy Hollow, New York for its annual street fair. The town is best known as the setting of one of America’s seminal ghost stories, The Legend of Sleepy Hollow by Washington Irving. However, Irving’s tale was written well before cars dominated transportation.
While sitting in bumper-to-bumper traffic, Lee Dillion, an ER nurse and a Headless Horseman rider has a choice to make. She can either sit for another hour with only two miles to go, or ride into town and make her gig on time.
Ever the self-described daredevil, Dillon and her team ready her stunning black Friesian named Eagle. Dillion exits the truck in her Headless Horseman costume and trots along a busy Route 9. The motorists stuck in traffic are getting way more than they bargained for on this busy day, as a Headless Horseman himself speeds past to Sleepy Hollow.
“People in their cars were going absolutely nuts,” Dillon, tells Popular Science. “It was great.”
The horse-human bond
Dillion, who is also the owner of Corinthian Equestrian Center in nearby Warwick, has been one of a handful of brave riders around the Hudson Valley who brave this ghoulish costume, jump up on their horses, and portray the area’s most famous undead resident for the past seven years. What started out as a Halloween gag with her son Luke, has turned into a special seasonal side hustle for Dillon and other riders. You can spot the Headless Horseman at the annual Halloween parade, film festival, haunted farm attractions, various dramatic readings of Irving’s tale, and more. The Headless Horseman also leads off the popular Mickey’s Boo to You Halloween Parade at Walt Disney World Resort in Florida, in reference to the 1949 film The Adventures of Ichabod and Mr. Toad. That cartoon was one of Dillon’s inspirations.
“When I was a kid, I loved the Disney movie. I fell in love with the horseman…
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