Meet the Headless Horseman of Sleepy Hollow

Good morning. It’s Friday, and this weekend promises a thrilling encounter with a man who will take on the iconic role of the Headless Horseman in the very location that inspired Washington Irving’s famous tale. We will also delve into the reasons behind the alarming rise in violence within New York City’s juvenile jails.

Hugh Francis as the Headless Horseman
Credit…via James Logan

Before he became a legendary figure without a head, the Headless Horseman of Sleepy Hollow was not someone who had undergone major surgeries. He hadn’t experienced the trials and tribulations of racing against airplanes or vintage cars. However, Hugh Francis, the actor portraying this spectral character in the picturesque village of Sleepy Hollow, New York—just about 30 miles from the hustle and bustle of Midtown Manhattan—has a different story to tell. At the age of 89, he has two nearly new hips and a brand-new knee. “I’m running on used parts,” he humorously quips.

In a remarkable twist, Francis not only embodies the Headless Horseman but has also triumphed in a race against a World War I-era biplane and a classic Model T in Massachusetts. Tomorrow night, and again on Sunday, he will ride through the very site where the tale describes the Headless Horseman’s burial, right next to the grave of Washington Irving himself at the Old Dutch Church of Sleepy Hollow.

“Most people see this as just a man in a black coat riding a horse,” Francis reflects thoughtfully. Yet, for some spectators, the mystery deepens. They might ponder whether this notorious ghost really hurled that infamous pumpkin at Ichabod Crane, the gullible schoolmaster who faced heartbreak and terror during his fateful ride. Others may recall their high school English lessons, where teachers proclaimed “The Legend of Sleepy Hollow” and “Rip Van Winkle” as America’s earliest short stories, forever etching these tales into the fabric of American literature.