Take A Tour Of Sleepy Hollow, The Town That Embraced Its Spooky Legend
It’s Friday night football in the Hudson Valley town that renamed itself for a ghost story. The crowd quiets. A bell tolls ominously over the loudspeaker. A group of high school players comes onto the field, led by their mascot: a black-clad rider on horseback with no discernible head, made famous in Washington Irving’s “The Legend of Sleepy Hollow.” Now it’s time for kickoff for the Sleepy Hollow Horsemen.
Lead image: Leora Dillon performs as the Headless Horseman during the Twilight Village celebration at Philipsburg Manor in Sleepy Hollow, New York, on Oct. 18. (Matt McClain/For The Washington Post)
A portrait of “Legend of Sleepy Hollow” author Washington Irving at Sunnyside, his house in Irvington. (Matt McClain/For The Washington Post)
Irving’s books are still on the shelf at the house he bought in 1835. (Matt McClain/For The Washington Post)
His desk is still on display. (Matt McClain/For The Washington Post)
Museum educator Nell Sirotin at Sunnyside, a National Historic Landmark. (Matt McClain/For The Washington Post)
Museum educator Mary Ellen D’Andrea wears a cameo depicting Irving. (Matt McClain/For The Washington Post)
Irving came to the region as a teenager to escape yellow fever in New York City and later settled there. He fell in love with the beauty of the landscape and the people who lived there, says Elizabeth Bradley, who leads programs and engagement for Historic Hudson Valley.
His famous story named actual places and people. That gave it authenticity combined with “the mythology … he had learned or imbibed as a child,” Bradley says, that lends “this kind of vividness and this reality that has clung to it today. That’s why more than 200 years later people still come looking for the Headless Horseman.”
Irving saw the old cottage as a teenager. He added the numbers 1656 when he remodeled it. (Matt McClain/For The Washington Post)
Visitors along Beekman Avenue in Sleepy Hollow on Oct. 16. On the sidewalk, a shadow? Or a ghost? (Matt McClain/For The Washington Post)
At the Old Dutch Church, a tree grows around a tombstone. (Matt McClain/For The Washington Post)
Morgan Bramwell poses for a photo outside Sleepy Hollow Bookshop on Oct. 17. (Matt McClain/For The Washington Post)
Philipsburg Manor presents a re-creation of an 18th-century colonial manor with an emphasis on the lives of enslaved people there. (Matt McClain/For The Washington Post)
Leora Dillon, a trauma nurse and also owner of the Corinthian Equestrian Center in Warwick, New York, is the official Headless Horseman of Sleepy Hollow. It’s very hard to see when riding at breakneck speed on horseback in a costume that covers your head. “You’re in a tunnel,” she says.
She relies heavily on her horse and their connection to safely maneuver during performances. “It’s not easy to do, especially if you want to do it right and perform,” says Dillon, but she loves seeing people’s reactions. “It cracks me up, it amazes me. It makes me smile.”
From left, Aunaly Palmer, left, Dillon and Payton Conklin watch the first half of the Sleepy Hollow High School football game as Dillon waits to perform again with her horse, Eagle. (Matt McClain/For The Washington Post)
Dillon and Eagle gallop across the field at halftime. (Matt McClain/For The Washington Post)
People are indeed still looking for the horseman, packing sidewalks and sold-out events throughout October. The actual town from the story was North Tarrytown until 1996, when town leaders changed the name to Sleepy Hollow to draw more tourists following the closure of a General Motors assembly plant.
A visitor passes by pumpkins at the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson on Oct. 15. (Matt McClain/For The Washington Post)
Angela DiMeglio performs with fire as part of Twilight Village at Sleepy Hollow at Philipsburg Manor on Oct. 18. (Matt McClain/For The Washington Post)
A lit tree along the Old Albany Post Road at Van Cortladndt Manor. (Matt McClain/For The Washington Post)
Historic Hudson Valley manages several historic sites, including Irving’s Sunnyside home that he purchased in 1835 and Philipsburg Manor, along with events that lean heavily on the legend. There’s an annual display of intricately carved pumpkins, and a dramatic outdoor retelling of the tale with lights and smoke. It ends, of course, with a headless rider in black, galloping on a black horse.
Wyatt Bloom, 9, stands next to a costumed performer at the Headless Horseman’s Hideaway on Oct. 15 in Croton-on-Hudson. (Matt McClain/For The Washington Post)
Jonathan Kruk performs “Irving’s Legend” at Sunnyside on Oct. 17. (Matt McClain/For The Washington Post)
A display of Ichabod Crane fleeing the Headless Horseman on Oct. 15 in Croton-on-Hudson. (Matt McClain/For The Washington Post)
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