While conducting the requisite research for “Eerie Rider: The Headless Horseman’s Forays into Pop Culture” (the Bonus Essay included in my eBook The Legend of Sleepy Hollow: Ultimate Annotated Edition), I strove to read every work of fiction that drew upon Irving’s classic short story. Any attempt at completism, though, was fated to be outdated, as new Sleepy-Hollow-related books and stories have continued to be published since the composition of my essay. One such example can be found in the 2022 anthology Classic Monsters Unleashed:

“Hacking the Horseman’s Code” by Lisa Morton

Halloween expert Lisa Morton gives a technological twist to the traditional tale of holiday terror (as she does in her 2018 story “The Ultimate Halloween Party App”). Mayor Gil Jankowitz is determined to turn the town of Oak Crossing into a modern-day Sleepy Hollow this tourist season. From a cutting-edge corporation called Advanced Mechs, Gil leases an artificially-intelligent, robotic replica of the Headless Horseman (to be employed as a roaming haunted attraction). This Horseman comes equipped with a supply of throwable, biodegradable jack-o-lanterns; upon programmed command, he can rear up, draw his sword, gallop about, and target a bystander for a pumpkin-head hurl. The problem, though, is that this mechanized simulation is too realistic in appearance and lifelike in behavior; Sleepy Hollow’s resident Hessian specter relocates to the uncanny valley. Naturally, the course of events take a dire turn as the AI consciousness continues to evolve, and the Horseman ends up doing more than just popping townspeople’s eyes.

The reader can easily guess where the story is headed (Morton perhaps gives too much away with her choice of title), but the ride itself thrills nonetheless. “Hacking the Horseman’s Code” is the quintessence of grim fun. Man, oh man, any town sporting a Headless Horseman who races through the neighborhood on October nights is a place where I am dying to live.