Finding Washington Irving's Headless Horseman: A Sleepy Hollow Tour

Washington Irving immortalized the legendary towns of Sleepy Hollow and Tarrytown in his 1820s short story The Legend of Sleepy Hollow. On this driving tour, you’ll chase down the ghostly and headless figure on horseback from the story, while you take in the iconic and haunted sites that inspired it.

Our drive starts outside Philipsburg Manor where you’ll hear how the famed author mixed Sleepy Hollow lore, local characters, and material he collected, borrowed, and stole from a range of sources to create the legend of the Headless Horseman. From there, I’ll show you the mill where a young Irving first heard the tale of a Hessian soldier who lost his head during the American Revolution. It was here, too, that the galloping goblin later raced and, using his detached head, brained schoolmaster Ichabod Crane. You’ll hear stories about the many spirits that are still believed to inhabit the town and its neighbor, Tarrytown, before ending at the site where the soldier is said to have lost his head!

On this driving tour through the Hudson River Valley, you’ll also:

• Find out what the 1685 Old Dutch Reformed Church graveyard has to do with the Headless Horseman
• See Sleepy Hollow Cemetery where Washington Irving is buried, and hear the ghostly tale of the Bronze Lady
• Pass through the often eerie roadways of Sleepy Hollow Country Club which are known stomping grounds for the galloping goblin
• Cruise by Sparta Cemetery which was scarred by British cannons during the American Revolution and now is haunted by the mysterious “Leatherman”
• Find out about the British spy, Major John Andre, who haunts Tarrytown’s Patriot’s Park
• Hear heart-breaking tales about the three Wailing Women whose cries penetrate storms
• Discover the other legend of Sleepy Hollow, Mother Hulda
• Take in the historical site of the author’s former home, Washington Irving’s Sunnyside
• Learn the name of the headless soldier that inspired countless iterations

Join me, Jonathan Kruk, Historic Hudson Valley’s “best storyteller”, as I show you the area’s most haunted spots. I’ve performed “the Legend” a thousand times in the last twenty-five years and look forward to bringing Irving’s stories to life on this tour. By the end of this hour-long tour, you too will be under Sleepy Hollow’s spell!