Franz Potter, a professor at National University who specializes in Gothic studies, says the headless horseman, as a supernatural entity, represents a past that never dies, but always haunts the living.
“The headless horseman supposedly seeks revenge—and a head—which he thinks was unfairly taken from him,” Potter says. “This injustice demands that he continually search for a substitute. The horseman, like the past, still seeks answers, still seeks retribution, and can't rest. We are haunted by the past which stalks us so that we never forget it.”
As for folklore mixing with history when it comes to the character of Ichabod Crane, The New York Times reports an actual Col. Ichabod B. Crane was a contemporary of Irving who enlisted in the Marines in 1809, serving 45 years. But there’s no evidence that the two ever met, according to the newspaper.
America’s first ghost story, Bradley says, has endured because it accommodates the changing American imagination.
“It inspires people because it reminds them that there are still some American mysteries, some half-truths that may never be fully known—and that's the whole point," she says. "The ‘Legend’ lends itself to any interpretation, and it continues to fascinate and terrify us in the best possible way.”