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How Sleepy Hollow brought its own legend to life

6 56
30.10.2025

Two centuries after Washington Irving wrote The Legend of Sleepy Hollow, the once-industrial town of North Tarrytown has rebranded itself around his ghostly horseman – and discovered that myth still sells.

It was early October in Sleepy Hollow, New York, when I saw the Headless Horseman for the first time. He burst from the tree line on horseback and parted the fog as he galloped towards me, his cloak billowing behind him – a giant spectre in the dark night.

After a couple of laps around the show's mock graveyard, the crowd cheered as the Horseman trotted over. Tonight's rider, a woman, welcomed everyone to pet her horse, a rescue named Eagle. As I gave Eagle a scratch, people lined up for tarot readings, vendors sold art and oddities at a pop-up market beside the barn and a roving band paraded through the grounds. This was Twilight Village at Philipsburg Manor – one of Sleepy Hollow's many immersive Halloween events.

The next night, I saw the Headless Horseman again at Irvington's 'Legend' at Sunnyside, a storytelling performance at American writer Washington Irving's historic home. I saw the Horseman everywhere else too: on street signs and police squad cars, on t-shirts and storefronts and even on the Christmas ornament I bought as a souvenir.

But I wasn't here for the spooky sights; I'd come to learn how a fictional place could transform into a real one – and how one story reshaped an entire town.

Few places in the United States are as entwined with a single story as Sleepy Hollow. Immortalised in Washington Irving’s 1820 tale The Legend of Sleepy Hollow, the town became synonymous with its ghostly rider – the Headless Horseman – and helped shape early American gothic fiction. The legend grew from Hudson Valley folklore and has since inspired countless retellings in film, literature and popular culture. With social media, increasing numbers of travellers have discovered that Sleepy Hollow, just a 50-minute train ride north of New York City, is a real place they can visit. But few know that the Halloween hotspot wasn't always called that – and for much of the 20th Century, it was better known for building cars than for ghost stories.

How Sleepy Hollow got its name

It's a common misconception that Irving coined the name, but it actually predates him by more than a century, with Dutch colonisers in the 1600s referring to the village as "Slaepers' Haven" and "Slaepers' Hol". The anglicised version, "Sleepy Hollow", was used informally in the region from then on.

Between 1870 and 1996, the town was officially named North Tarrytown. When the General Motors plant that had operated in the area for a century closed in the mid-1990s, residents were forced to reimagine their town's future. Seeing the need for a rebrand, they voted in favour of changing the name to Sleepy Hollow.

The rebrand worked and the town embraced its new identity. The Headless Horseman became the town's unofficial mascot – and the official mascot of the local high school. But while locals expected some tourism with the new moniker, they didn't foresee just how completely their town on the Hudson River would transform into a Halloween pilgrimage site.

Across the street from Philipsburg Manor sit three of Sleepy Hollow's most famous attractions: the

© BBC