The Upstate Legend of Sleepy Hollow
Tucked amongst the rolling hills of the Hudson Valley lies a place where the air hums with an old-world magic and a touch of eerie, spooky charm. This is the backdrop for one of America’s most timeless ghost stories... Washington Irving’s The Legend of Sleepy Hollow. The tale runs so deep through the region’s history that it’s nearly impossible to visit Tarrytown and Sleepy Hollow without sensing the ghostly presence of the Headless Horseman himself!
Irving describes Sleepy Hollow as a place of "drowsy, dreamy influence," where the woods are deep and shadowy, and the silence is broken only by cawing of crows. Traveling through this part of upstate New York today, you can still catch that atmosphere, especially on an autumn afternoon when a mist rises from the Hudson. The Old Dutch Church and its burial ground, which feature prominently in the story, still stand as they have for centuries.
At the heart of the story is the conflict between the superstitious schoolmaster, Ichabod Crane, and the local hero, Brom Bones. Their rivalry over the beautiful Katrina Van Tassel culminates in Ichabod's infamous ride home from a harvest party, a journey that takes him through the most haunted hollow. It is here that he encounters the spectral figure, a Hessian soldier from the Revolutionary War who lost his head to a cannonball and now rides forth in search of it. The terror of that chase is a masterpiece of American folklore, and Irving leaves the fate of Ichabod Crane deliciously ambiguous, allowing for the possibility that the Horseman was nothing more than a clever prank by Brom Bones.
This legend has become a major part of the area's identity. While upstate New York has many beautiful and historic places, from the Catskill Mountains to the Erie Canal, the villages of Tarrytown and Sleepy Hollow have embraced their famous folklore. You can visit historical sites mentioned in the story, and the community celebrates its spooky heritage, especially during the Halloween season.
Things to do in the Sleepy Hollow area:
Visit the Old Dutch Church and Burying Ground, the historic site that served as the real-life setting of Ichabod Crane’s final, fateful ride. Wander among the centuries-old gravestones and imagine the eerie atmosphere that inspired Washington Irving’s classic tale!
Tour Sunnyside, Washington Irving’s charming riverside home. Explore the house and gardens that reflect the life and times of one of America’s most beloved authors.
Explore Sleepy Hollow Cemetery, a sprawling and beautifully maintained historic cemetery where Irving himself is buried. Discover the graves of local figures, soldiers, and other historic residents while soaking in the quiet, contemplative atmosphere.
Experience the Great Jack O’Lantern Blaze, one of our most favorite events! An unforgettable autumn event where thousands of hand-carved pumpkins light up the night in intricate displays.
Take the Horseman’s Hollow walking tour, a haunted trail through the woods and streets of Sleepy Hollow that brings Irving’s ghostly legend to life. Guides share the history, folklore, and creepy tales of the area for a truly immersive experience.
Stroll through downtown Tarrytown, a beautiful village full of historic buildings, cozy cafés, boutique shops, and amazing views of the Hudson River. Take your time to explore the streets, enjoy local treats, and soak in the charming atmosphere that blends history and modern life.
