The Legend of Sleepy Hollow is the Halloween tale I hold nearest and dearest to my heart. For as long as I can remember, each Halloween, I curled up on the couch with my family and watched the Bing Crosby-narrated Disney version. We also reserved one pumpkin every year to carve into the ghoulish Headless Horseman. When I was old enough, I began my tradition of reading Washington Irving’s short story on Halloween Eve, that is continue to this day. I even defended Brom Bones in a sixth grade mock trial and got him acquitted (to this day, I still can’t tell you how I pulled this off).

So what is it about this tale that brings readers, like me, back every Halloween for more? Is it the dreamy pastoral town of Sleepy Hollow, with its quaint residents, candlelit parties, and bone-chilling ghost stories? Is it the mystery of what really happened to Ichabod Crane on the covered bridge? Is it the faint possibility that the ghost of a Hessian soldier scours the land in search of a head?

I think it’s that Washington Irving is a literary genius, who knew how to blur the lines of reality and imagination just so. Before publishing The Legend of Sleepy Hollow, he began spinning a story about Diedrich Knickerbocker, whose surname eventually became synonymous with New Yorkers. Diedrich Knickerbocker was a character who appeared in many of Washington Irving’s works, including some of his earliest, published in the Morning Chronicle. The genius behind the invention of Diedrich Knickerbocker is the layer of mystery he adds to some of Irving’s works. In The Legend of Sleepy Hollow, Diedrich Knickerbocker is ominously mentioned at the beginning of the story:

“Found among the papers of the late Diedrich Knickerbocker.”

Before publishing The Legend of Sleepy Hollow, Washington Irving anonymously published an advertisement in the Morning Chronicle reporting that Diedrich Knickerbocker had gone missing. A few weeks later, Irving published another anonymous announcement, claiming to have found a disheveled man wandering the countryside near Tarrytown and Sleepy Hollow, whose description matched that of Diedrich Knickerbocker. Shortly thereafter, Irving published The Legend of Sleepy Hollow using while the mystery of Diedrich Knickerbocker continued to loom over New York.

If the printed story of the Headless horseman was found among Diedrich Knickerbocker’s works, does that make him the narrator? Of course, this does not mean the Knickerbocker himself wrote the story, so perhaps its contents so frightened Knickerbocker that he left his home with great haste to escape the Headless horseman. Perhaps one can think of Diedrich Knickerbocker as an Ichabod Crane in his one right – a scholarly stranger who discovered the secrets of Sleepy Hollow.

For me, it is the romantic mystery of Diedrich Knickerbocker and The Legend of Sleepy Hollow that brings me back every year. I don’t know if I would be relieved or disappointed to discover the truth of what happened to Ichabod Crane. The possibility of haunts and spooks still excites and terrifies me as much as it did when I was a little girl. My heart still races as Ichabod and Gunpowder tiptoe home from the Van Tassel party; I still get goosebumps from the story’s haunting last words:

“The schoolhouse being deserted soon fell to decay, and was reported to be haunted by the ghost of the unfortunate pedagogue and the plowboy, loitering homeward of a still summer evening, has often fancied his voice at a distance, chanting a melancholy psalm tune among the tranquil solitudes of Sleepy Hollow.”

Eat: Doughty Doughnuts

Drink: Van Tassel’s Apple Cider