Set on the eastern banks of the Tappan Zee, Hudson River it is now known by, sits a small town that is a stone’s throw away from the bustle of the center of the world, New York City. That town, known since the American Revolution as Tarrytown, has a northern hamlet that acquired a more appropriate name in 1997 to match its folklore beginnings, Sleepy Hollow. Just the name evokes feelings of warmth and mystery—the lingering ghosts of the stories and traditions that came before. Sleepy Hollow is most famous for its legend penned by one of the first great American authors, Washington Irving. Kids grow up hearing the tales of the Headless Horseman who rides at night, head tied to his saddle and throwing jack-o-lanterns at his victims, chasing down the very unlucky Ichabod Crane. This tale has been retold in movies, most famously by Tim Burton, in Disney animation, and alluded to in other works since its inception in 1819.
In the Northeast, Halloween is usually synonymous with Salem, Massachusetts—the town whose dark history of witch hunts and executions crowd the air. New England’s spooky history is all well and good, but about three hours south, I think you’ll find a more intimate relationship with dark tales and the holiday. And to set the record straight, New York is not part of New England. They are two separate regions separated by the Connecticut border. Each year families, myself included, make the trip to partake in all the offerings Historic Hudson Valley has to delight all your spooky whims.
From street fairs to the scarecrow crawl to the nightly telling of The Legend, Tarrytown/Sleepy Hollow is the perfect place for your spooky season trip with fewer crowds than our northern neighbors. We even have witches too! (And Imps and Goblins). To best articulate why this region is the perfect spot, I went to the best source I could, Johnathan Kruk— a local storyteller and performer who tells the Legend of Sleepy Hollow every year in the courtyard of Washington Irving’s home. He has been performing The Legend for twenty years and is a can’t miss every season but snag your tickets early because they do sell out. His blend of storytelling, accompanying sound effects, and music create an eerie atmosphere as you sit by the Hudson River watching the sunset, complete with a special appearance by the Headless Horseman himself.
I asked him what makes this region such a special melting pot for ghostly activities, and he replied that “the ghosts are meant to remind us of what came before, telling us stories and peeling back the layers.” He went on to describe the region geographically too, in the shadows of the Adirondacks and south of them, the Catskill Mountains, the landscape embraces you, and it holds you in an almost tomb-like embrace. While the pilgrims first landed in Massachusetts, the Hudson River and this lower Hudson Region were named the “key to the revolution” by both the British and the Rebels during the war. From the early days of settlement, you peel back the layers and reveal rich folklore. From the Indigenous tribes warning the Dutch to turn back or the imps of the Tappan Zee, to the stories of the revolution, Benedict Arnold, and the hanging of John André. Some say his ghost can be seen wandering the border of where Sleepy Hollow meets Tarrytown. When Washington Irving moved to the region as a young man, he had all these stories informing him. The same year The Legend of Sleepy Hollow was written, Mary Shelly wrote Frankenstein, arguably two of the most influential and important pieces of this new age of literature.
The Headless Horseman is said to be a Hessian (British) soldier who had his head shot off with a cannon during the war. While the story of Crane and the Van Tassels is entirely Irving’s creation, the specter of a red coat coming back for revenge was a frightening thought only twenty years after the revolution. But the idea of these creatures, the horseman and even Frankenstein’s monster, created out of legend and strife, scare us because they are searching for a life to take hold of. To be free from their shackles of death. That’s why these stories still resonate today. The idea of something coming to take our personhood away from us is a frightening thought that we often face in the horrors of real life.
While the original bridge from Irving’s story is no longer standing, you can visit the one built in its place, which sits inside Sleepy Hollow Cemetery. The cemetery offers tours, or you can opt to guide yourself, but remember to be respectful as it is still a working cemetery. There are two sections, the southern part connected to the Old Dutch Church, where the unmarked grave of the real-life Mother Hulda sits, and the northern part, which is Sleepy Hollow Cemetery and not affiliated with the church.
Washington Irving and his family have a grave plot here, along with the Rockefeller and Carnegie families. The bridge is tucked down a path away from the graves but completely accessible, and it’s really a beautifully serene spot with a babbling brook running beneath it. Johnathan Kruk has a haunted self-guided tour on voice maps that can take you to all the alleged haunted locations around town. His off-beat recommendation, which most folks don’t know, is the Tarrytown Music Hall. He says the “projectionist hanged himself in the ’70s, his ice skates and coffee mug remain in place”, which you can view on a guided tour.
People travel miles to see the real spectacle of the season —The Great Jack-O-Lantern Blaze, hosted at Van Courtland Manor by Historic Hudson Valley. This event brings together over 7,000 hand-carved pumpkins themed to a myriad of topics that light your path as you walk the grounds. They recreate the New York skyline, form shapes of animals and marine life, bridges and tunnels you can walk through as the lights from the jack-o-lanterns dance around you. It is truly a spectacle.
Of course, there are also the manor homes: Kykuit, the Rockefeller Estate; Lyndhurst Mansion and Philipsburg Manor. All are haunted and open for tours. You can even visit Washington Irving’s house during the day, I suggest following that up with The Legend at night. We are a small but mighty region, and the foliage is unlike anything else. So please come to Sleepy Hollow, walk the town, and take in all our shops, dining, and experiences while you peel back the layers of history. And if you’re looking to dive further into the lore of the region, Johnathan has written an incredible book collecting the lore of the Hudson Valley titled Legends and Lore of Sleepy Hollow and the Hudson Valley. Happy Haunting Ghouls!
Get your advance tickets to The Legend right here.
