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I’m driving through the Philipse Manor neighborhood in Sleepy Hollow, N.Y., to collect my daughter from her friend’s house when a blood-curdling shriek meets my ears. Across the street, a large black horse paws the ground, agitated — yet the animal’s rider remains eerily still. The cloaked horseman is missing a very important appendage.
As the setting for Washington Irving’s famous legend, Sleepy Hollow has become one of the most iconic Halloween destinations in the country, and the headless Hessian soldier appears everywhere from local parades to the high school’s homecoming game. I’ve lived in neighboring Tarrytown for 20 years, but even I get the shivers come October — catching a glimpse of the decapitated spirit on horseback never gets old.
Overlooking the majestic Hudson, just 20 miles north of New York City and near the Tappan Zee Bridge, Sleepy Hollow and the surrounding towns host myriad daytime and evening Halloween activities — from the whimsical to the downright terrifying — offering visitors and locals alike multiple ways to savor the spooky season and see the legend come to life.
Kick things off a few miles south at Sunnyside, Irving’s riverfront home, which he described as “a little old-fashioned stone mansion, all made up of gable-ends, and as full of angles and corners as an old cocked hat.” The author spent the last years of his life in this enchanting storybook cottage that even had its own railway station on the banks of the Hudson. Perfect for those with a lower fright threshold, autumn tours of Sunnyside introduce Irving’s life and legacy while revealing inspirations behind the prolific writer’s most famous tale. Children will love watching a shadow puppet performance of “The Legend of Sleepy Hollow” and joining a scavenger hunt throughout the bucolic grounds.
Tombstones at Sleepy Hollow Cemetery
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Right in the heart of Sleepy Hollow Village, the Old Dutch Church, built in 1697, remains one of the oldest in the country, and the graves of the locals who influenced Irving’s characters can be found within its historic burying grounds. You won't find the final resting places of Ichabod Crane or Abraham “Brom Bones” VanBrunt among the tilting 18th-century markers, but you will come across the grave of Eleanor Van Tassel Brush, whom Irving purportedly modeled Katrina Van Tassel, the legend’s coquettish debutante, after. Eleanor’s aunt, Catriena Ecker Van Tassel, is also buried here.
Come nightfall, master Hudson Valley storyteller Jonathan Kruk regales audiences with theatrical performances of Irving’s Legend accompanied by dramatic, live organ music and the flicker of candlelight.
Daytime visitors can wander nearby Sleepy Hollow Cemetery’s foliage-filled landscape that's complete with elaborate mausoleums and haunting tombstones. Irving himself rests here along with other notable figures like Andrew Carnegie, Elizabeth Arden, Samuel Gompers and William Rockefeller. Evening lantern tours provide an especially hearty dose of All Hallows spirit. While in the Washington Irving Chapel, local author-actor David Neilsen offers a spine-tingling reading series featuring the short works of Irving, Edgar Allan Poe and others throughout the season.
Bridge to Philipsburg Manor
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At the historic restoration of Philipsburg Manor, evenings find thrill seekers winding down a lantern-lit path to a ghostly hamlet haunted by the headless Hessian himself. The macabre of every variety — gory ghouls, a harrowing corn maze, tormented villagers gone mad — accompanies the journey to the final destination, Ichabod Crane’s schoolhouse, where visitors may meet the same fabled fate as Irving’s lanky schoolmaster.
Far less creepy and new for this season are evening screenings of an original silent film titled The Unsilent Picture, inspired by Irving’s curious tale, “The Adventure of the Mysterious Picture.” Starring Bill Irwin, live musicians and sound effects created by an in-person Foley artist bring a dynamic energy to the event.
