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 and thought it was just the coolest thing,” says Dillon. “When I was probably 10 or 11, I said that one of these days I’d get a big black horse and be the Headless Horseman.”
[Related: Why do we see ghosts?]
However, accomplished and enthusiastic riders like Dillion are only one member of the team behind this spooky spectacle. It’s the horses, with their imposing height and power who make this possible. And yes, the horses can get a little spooked themselves.
“Horses have a very finely tuned fight or flight reflex and I always think it’s pretty amazing that they even let us do the things that we do to them, like ride them or keep them in pens,” Cornell University College of Veterinary Medicine equine veterinarian Michelle Delco tells Popular Science. “The truth is, if they really didn’t want to do these things, they wouldn’t. But they trust us. It’s as if they understand that there’s a partnership going on.”
Horses are incredibly intelligent animals, but generations of breeding have influenced what horses are most prolific. According to Delco, this partnership goes back thousands of years, when groups of wild horses began to interact with early humans, much like the way dogs were domesticated.
“We have selected individuals of the species over time that are curious about humans,” says Delco. “They’re the ones in the herd that let us approach them or were brave.”
In that time, the bond has helped humans farm, in warfare, travel, and provided sport, recreation and entertainment. A well-trained horse can be similar to a bike, stopping like a handbrake almost instantly when the rider gives the proper commands. Still, they are animals that can be unpredictable, so it is up to the riders to set a calm and confident tone.
“When you’re riding a horse in a parade or anything like that no matter how close your partnership is, it’s sort of the human’s job to never become complacent,” says Delco. “The human must always remember that it’s not that a horse really ever wants to hurt you or another person. It’s just hardwired into their genes that they’re gonna react. They may sort of have a reaction no matter how well trained they are.”
Bomb proofing for real world spooks
For parades and events like the spooky happenings around Sleepy Hollow, riders are generally looking for specific traits.
“I need a horse that’s intelligent, trusting, and learns,” says Dillon. “It needs to learn to trust that I’m not going to get them in trouble. I also need to trust them to see for me. Also good feet and good gatedness on them. Their gates show that they are powerful and majestic.”
In the short story, Irving writes that the specter, “appeared to be a horseman of large dimensions, and mounted on a black horse of powerful frame,” so darker hued horses are preferred for the sake of literary accuracy. Dillon uses Eagle and a fellow Fresian named Falcon, who will be in the annual Halloween parade on October 26th. Both are formidably dark and very sweet, especially when apples or carrots are around.
When in costume, Dillion can barely see in front of her, and primarily relies on her horse to get maneuver safely. She can see their ears and follows along.
“I don’t have to really have to hear because my horse’s ears tell me exactly where everybody is, because their ears are their satellites,” says Dillion. “Their hearing and their vision is three to four times what ours is. I’m watching him because he’s telling me where the crowd is.”
Horses are a prey animal, so to survive in the wild, they evolved finely tuned senses. To work with those senses and gain enough trust and ease to bring a horse into a more uncontrolled environment, riders use a training technique called bomb proofing. The rider will slowly work to desensitize the horse to various sounds and stimuli. The training process can look different depending on the type of event.
[Related: How horror movie soundtracks prey on our fears.]
“Somebody will have a scarf and wave it in front of their face. Then it becomes something bigger like a plastic bag that makes noise and waves around,” says Delco. “Then, somebody will grab a tarp. So you very gently increase the stimulation and the weirdness and the sounds.”
One of the events that Dillon participates in is a haunted Boo Barn at Thunderbird Farms in Goshen, New York. The Boo Barn features not only Dillon as the Headless Horseman, but various jumpscares and scary characters wielding chainsaws. According to Dillion, the horses don’t like the chainsaw sounds in particular. A few weeks before the Halloween season, she works with Eagle or Falcon to get them used to the jarring sounds of the saws.
“When you’re on the horse, you have your legs around the horse and you have your hands on the reins. They’re connected to their mouth,” explains Dillon. “For horses that are not experienced, if you’re afraid, then they think they have to be afraid. If you’re confident the horse will be confident. If you are not confident, they’re not going to go forward.”
Her “Ichabod” aka boyfriend Gerry or another rider from the equestrian center is also on hand to help manage the eager crowds who want to take a picture with the equine Halloween legend. During this year’s street fair, Eagle and Dillon posed for pictures for three hours with excited patrons.
‘It’s just another day at work’
Just like humans, different horses have strengths, weaknesses, and personalities, and will enjoy certain tasks more than others. A plow horse is not a show horse and a dressage horse wouldn’t make a good race horse.
“For that horse, it’s just another day at work,” says Delco. “They get to the point where they know that this is their job, and that they just, they really want to do their job. And some of them love to perform.”
When Eagle or Falcon see Dillion in that imposing costume, they get very excited and know what is coming.
“Eagle is so excited when I get in costume,” says Dillon. “He just blooms right up. He likes to gallop and go fast because he is super sound sensitive, super forward, and he loves it.”
Almost as excited as the crowd of spooky season enthusiasts ready to see one of Halloween’s most famous figures in the flesh.