The Headless Horseman Biography Flash a weekly Biography.

Ready for your Headless Horseman update, because apparently even decapitated 18th-century phantoms get busier every fall than my inbox after I tweet anything political. This week, the Horseman is everywhere—at festivals, on stage, even getting a few suspicious nods on TikTok that I’m fairly certain should come with a “parental advisory: nonsense” stamp.

On the real—not “real” real, but you know, the kind of real reserved for urban legends and awkward family gatherings—the Horseman’s been headlining at Conner Prairie’s Headless Horseman Festival, which wraps up tonight. Picture this: thousands of Midwesterners willingly chasing a guy with no head through haunted corn mazes and pretending axe-throwing is a valid solution to supernatural encounters. Somewhere, Washington Irving is facepalming. It’s practically the Super Bowl for the Horseman, minus commercials and with way more hayrides. This festival genuinely puts his legend right in the center of fall tradition—if he’s got long-term biographical significance anywhere, Indiana just made it official.

Meanwhile, over in Hudson Valley, the Horseman has achieved pumpkin influencer status at the Great Jack O’Lantern Blaze. I’m talking hand-carved likenesses, immersive whodunit theater, and a VIP “Horseman’s Hideaway” speakeasy experience. Guests snoop around Sleepy Hollow for clues about Ichabod Crane’s fate in a manner that would make even British murder mysteries raise an eyebrow. If you think influencers with ring lights are over the top, just wait until you see a ghost story glow up via 10,000 pumpkins.

Elsewhere, okay, on the West Coast, Oceánica Ballet in the Bay Area is reprising its “Headless Horseman + Viva La Vida” for another spooky run. They’re exploring the legend through dance—yes, ballet—and the Horseman’s transformation from terror to tragic outsider. I’d make a joke about him pirouetting off his head, but honestly, the reviews are glowing. Apparently, nothing says “family-friendly” quite like ghostly puppetry and existential dread.

On social media, the Horseman's been trending again—predictably, every time someone spots a shadowy rider on a horse in upstate New York, Twitter lights up with “Is the Headless Horseman real?!” The only thing more fictional than the Horseman is the idea that the internet will ever be chill.

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See you next time—hopefully with my head still attached.

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