Our Q&A With Westchester’s Own Headless Horseman

The principal performer at Historic Hudson Valley’s annual fright fest, Horseman’s Hollow—a live-action haunted-house experience inspired by “The Legend of Sleepy Hollow”—returns this month to the Philipsburg Manor historic site in Sleepy Hollow. The Horseman, who prefers to remain anonymous, tells us about the joys of terrorizing visitors, and the technical skills that got him the job.  


Q: How long have you been playing the Horseman?

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A: I have done various film gigs on my stunt horses. Years ago, when the staff at Historic Hudson Valley decided they should raise the bar on their show at Philipsburg and make it a major extravaganza, they contacted me to spice things up. As a professional horseman, I have studied Revolutionary Era horsemen, so this role was a slam dunk!

Q: How does the whole “headless” part work? 

A: I only have a very limited peek at the world through the fabric and must rely on the horse for most of the up-close action. I usually walk the venue carefully before a show to ID any danger areas and emergency exits and try to get any danger zones cleared. My biggest nightmares are audio wires and [stanchions placed to control crowds].

Q: Do those challenges take away the fun for you?

A: Because of the conditions, the ever-changing role requires some very particular equine expertise and a specially trained horse, but it’s a blast night after night. It’s really enjoyable to see the audience get such a thrill from seeing me.

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Q: What are those reactions like?

A: It’s a giddy kind of fear, a fun fear, but also for many it’s like seeing a Halloween rock star. I’m a popular photo op. I’ve photo-bombed many a selfie. TV gets boring and folks love a change of pace. People are tired of all the over-the-top events and special effects and love the presence of a real, live horse and horseman.

 Q: How many people know your real identity?

A: A very chosen few: my agent, my costume mistress, a secret double, and my support crew. It’s a closely guarded impression meant to maintain the highest standards of authenticity while promoting the ‘Legend.’

Q: Do you live in the county? 

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A: I live happily on my 50-plus-acre Fox Forest Farm in Greenville, New York. At night, I roam cemeteries and look for fresh victims. [Just kidding.]

Q: Are you a Halloween fanatic?

A: I ride a horse in an elaborate Headless Horseman costume every weekend in October for hours each night…can the answer be anything but ‘yes’? 


Our Best of Westchester Party is July 24!

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

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