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Each year, on the first Saturday of October, the quaint village of Sleepy Hollow, New York, attracts a multitude of visitors for its much-anticipated street fair. This charming town is famously recognized as the backdrop for one of America’s classic ghost tales, The Legend of Sleepy Hollow, penned by Washington Irving. Notably, Irving’s narrative predates the era when automobiles became prevalent.
Amidst a sea of halted vehicles, Lee Dillion—a dedicated ER nurse and an enthusiastic participant in Headless Horseman festivities—faces a dilemma. She can either endure another hour stuck in traffic with only two miles remaining or gallop into town to ensure she arrives on schedule.
Embracing her adventurous spirit, Dillion prepares her magnificent black Friesian horse named Eagle. Clad in her Headless Horseman attire, she dismounts from her vehicle and begins trotting along the bustling Route 9. The drivers caught in gridlock are treated to an unexpected spectacle as the Headless Horseman rides past en route to Sleepy Hollow.
“People were going absolutely wild in their cars,” Dillon shares with Popular Science. “It was fantastic!”
As traffic halts outside Sleepy Hollow, New York, Lee Dillion makes her entrance fully dressed for the occasion. CREDIT: Lee Dillon/Corinthian Equestrian Center
VIDEO: As traffic halts outside Sleepy Hollow, New York, Lee Dillion makes her entrance fully dressed for the occasion. CREDIT: Lee Dillon/Corinthian Equestrian Center.
The Connection Between Horses and Humans
Dillon is not just an avid rider; she also owns Corinthian Equestrian Center, located nearby in Warwick. For seven years now, she has been among a select group of daring riders from around Hudson Valley who don this eerie costume and embody one of literature’s most iconic spectral figures during Halloween festivities. What began as a playful Halloween activity with her son Luke has evolved into a cherished seasonal endeavor for Dillon and fellow equestrians. The Headless Horseman can be spotted at various events including an annual Halloween parade, film festivals , haunted farm attractions and dramatic readings inspired by Irving’s work.
Additionally,Mickey’s Boo to You Halloween Parade at Walt Disney World Resort features this legendary character prominently—an homage to Disney’s 1949 animated classic The Adventures of Ichabod and Mr.Toad. This cartoon served as one source of inspiration for Dillon’s passion.
“As a child I adored that Disney movie,” recalls Dillon fondly. “I was captivated by the horseman; he seemed so fascinating! I promised myself that someday I would own a large black horse and become him.”
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However remarkable riders like Dillion may be; they are just part of what brings this haunting performance alive—the horses themselves play an essential role with their impressive stature and strength while occasionally displaying their own nervousness amidst all excitement.
“Horses possess highly developed fight-or-flight instincts,” explains Dr.Michelle Delco from Cornell University College Of Veterinary Medicine.
“It’s astonishing how they allow us to engage them through activities like riding or confining them within stables.” She adds that if horses truly opposed these interactions—they simply wouldn’t comply—but instead they exhibit trust towards humans indicating mutual understanding exists between species.”
Horses are known as incredibly intelligent creatures whose breeding history has shaped their behavior over generations.
According To Delco ,this partnership dates back thousands Of years when early humans began interacting With wild horses similar To dog domestication .
“We have selectively bred individuals who show curiosity towards people,” says Delco .”These animals tend To be more approachable And courageous within Their herd.”
Over time ,the bond between humans And horses Has facilitated advancements In agriculture , warfare , transportation As well As providing recreation And entertainment opportunities .A well-trained horse Can respond almost instantaneously Like A bicycle stopping When given proper commands ; however They remain unpredictable creatures requiring Riders To maintain calmness And confidence throughout Their interactions .
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“When participating in a parade or similar event, regardless of the bond you share with your horse, it is crucial for the rider to remain vigilant,” explains Delco. “Horses are not inherently aggressive; their instincts drive them to react. Even the most well-trained horses can have unexpected responses.”
Preparing Horses for Real-Life Frights
During parades and events like those held in Sleepy Hollow, riders seek specific qualities in their horses.
“I require a horse that is smart, trustworthy, and capable of learning,” states Dillon. “The horse must trust that I will keep it safe while I also need to rely on its ability to perceive potential dangers. Additionally, good conformation and movement are essential; their gaits should reflect strength and grace.”
In Washington Irving’s tale, the author describes a ghostly figure as “a horseman of large stature mounted on a powerful black steed,” which is why darker-colored horses are favored for authenticity. Dillon rides Eagle and another Friesian named Falcon during the annual Halloween parade scheduled for October 26th. Both horses possess striking dark coats and gentle temperaments—especially when treats like apples or carrots are involved.
While dressed in costume, Dillon has limited visibility and relies heavily on her horse’s guidance to navigate safely through crowds.
“I don’t need my hearing much because my horse’s ears indicate where everyone is located; they act as my radar,” shares Dillon. “Their auditory perception and vision capabilities far exceed ours—by three to four times! I focus on him since he helps me gauge crowd movements.”
As prey animals,horses have evolved acute senses necessary for survival in nature. To build trust with these animals before introducing them into unpredictable environments, riders employ techniques known as bomb proofing. This method involves gradually desensitizing the horse to various sounds and stimuli based on the event type.
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“We start small—someone might wave a scarf near their face—and then progress to larger items like noisy plastic bags or tarps,” explains Delco. “The idea is to gently escalate exposure so they become accustomed to unusual sights and sounds.”
One notable event where Dillon showcases her skills is at the haunted Boo Barn at Thunderbird Farms, located in Goshen, New York. The Boo Barn features not only Dillon portraying the Headless Horseman but also includes various jump scares from characters wielding chainsaws—a sound particularly disliked by many horses according to Dillon’s observations. In preparation for Halloween festivities each year, she trains Eagle or Falcon weeks ahead of time so they can acclimate themselves with these startling noises.
‘When mounted,’ says Dillon,’my legs wrap around my horse while holding onto reins connected directly to its mouth.’ She adds,’For inexperienced horses, if you exhibit fearfulness then they will mirror that anxiety; however if you project confidence then your mount will feel secure enough to move forward.’
‘My partner Gerry—or another rider from our equestrian center—is always there too helping manage eager fans wanting photos with this iconic Halloween character.’ During last year’s street fair alone,Dillon posed alongside Eagle taking pictures with enthusiastic attendees for over three hours!
‘Just Another Day at Work’
‘Like humans,horses possess unique traits includingstrengths weaknesses,and personalities’,and some may prefer certain activities over others.A plowhorse isn’t suited as showhorse nor would dressage champions excel racing against thoroughbreds!
‘For these animals,this becomes just another workday’ remarks Delco.’They eventually recognize this role becomes part of who they are—and many genuinely enjoy performing!’
Dillon notes how both Eagle & Falcon become visibly excited upon seeing her donning an elaborate costume—they know what lies ahead! ‘Eagle lights up whenever I put it on’ she exclaims ‘He thrives off speed & loves galloping due his heightened sensitivity towards sounds!’
This enthusiasm mirrors that felt among crowds eagerly awaiting one of Halloween’s most beloved figures brought vividly alive before them!
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