It Came in the Night: Tarrytown and Sleepy Hollow, NY

As a kid, I liked to scare the crap out of myself. I stayed up late watching Are You Afraid of the Dark  between slotted fingers, clutching a pack of Gushers for protection. I devoured every eerie Goosebumps novel and bought every volume of Scary Stories to Tell in the Dark. Even as an adult, the chapter about the girl who gets a mysterious bite on her face which births hundreds of baby spiders still makes me want to take a shower. It all gave me nightmares, but the feeling of utter terror is the biggest rush one could get at eight years old, so I kept up the habit.

As we plotted our journey into upstate New York, I wanted to go to Tarrytown and Sleepy Hollow, birthplace of America’s most famous ghost story. The Legend of Sleepy Hollow was a favorite of mine as a young fan of horror-fiction. I owned a more “kid friendly” illustrated version, which depicted a pink-cheeked Katrina Van Tassel and her polarized suitors, the meat-necked Brom Bones and the lithe and unfortunately superstitious schoolteacher Ichabod Crane. A copy of the Disney adaptation, The Adventures of Ichabod and Mr. Toad, made its way into my rotation of frequently watched films, to the delight of my mother, who was sick of watching The Little Mermaid for the thousandth time.

It is a story that everyone knows - Ichabod Crane competes with local neanderthal Brom Bones for the hand of Katrina Van Tassel. At a party, while gathered in the parlor for a night of storytelling, Ichabod hears the legend of the Headless Horseman, a gentleman who had the misfortune of losing his head to a rogue cannonball during the War of 1812. In the spirit of wooing miss Van Tassel, Crane searches for the night rider, only to meet the “ghost” and have the fertilizer scared out of him. While the Disney version has a frightened Crane fleeing Sleepy Hollow, other versions end with Ichabod Crane being found dead the following morning. The reader is left to speculate whether Crane met his end at the hands of Brom, or possibly at the hands of the real Headless Horseman. 

The story is one of the earliest pieces of American folklore that is still read and appreciated today, and Tarrytown couldn’t be prouder. Its scribe, Washington Irving, was a life-long resident of the area. There are restaurants, statues, and street signs dedicated to the story, letting visitors known which concrete monument marks the “site” of the meeting between Mister Crane and the Headless Horseman.

Despite being only 15 miles from the Bronx, and all of 27 miles away from Times Square in Manhattan, Tarrytown is devoid of the bustle and endless motion that emanates from the City. The town, like nearly all of the rest of Westchester County in New York, retains its 18th-Century old-world charm.

We walked down the highway to Sleepy Hollow Cemetery, where Washington Irving is buried in a small plot with his entire family. Nearby, his postmortem neighbors include Louisa May Alcott and Brooke Astor. I thanked him for Sleepy Hollow, a keystone in my early descent into the literary world, and endless nights of checking inside my closet and under my bed.