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Just Where Was That “Sleepy Hollow,” Actually?

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October 3, 2017


by Barrett Seaman   

It is, of course, the name of a village in Westchester County—arguably the county’s most famous. It used to be North Tarrytown until administrators decided they’d get better recognition by taking advantage of that famous short story by Washington Irving. Practically everybody knows of The Legend of Sleepy Hollow, Irving’s fantastical tale of a headless horseman, said to be the ghost of a Hessian soldier decapitated by a cannonball during the Revolutionary War, who chased after a gangly schoolteacher named Ichabod Crane in the dead of night after a party.

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P.16-BRIDGE sleepy hollow etchingCrane, so the story goes, was in amorous pursuit of one Katrina van Tassel, the fetching daughter of a prosperous local farmer, and was on his way home from a party at the van Tassels’ Tarrytown home when a ghastly apparition confronted him and chased him through the darkened hills of the Hudson Valley. At the end of this horrifying ride, the monster hurled his head (actually a pumpkin) at the hapless schoolteacher. Crane was knocked from his horse but lived, though never to be seen again in the area. By Irving’s strong implication, the “ghost” was really another Katrina suitor, the swaggering young Dutchman Abraham van Brunt, known as Brom Bones.

But where exactly did all this take place (assuming, of course, that it took place at all)? Irving gives his readers a few tantalizing clues. He tells us that it happened “…perhaps about two miles” from Tarrytown in “a little valley, or lap of land, among high hills, which is one of the quietest places on earth. A small brook glides through it.” This “sequestered glen,” we are told, “has long been known by the name of Sleepy Hollow, and its rustic lads are called the Sleepy Hollow Boys throughout all the neighboring country.”

Miriam Webster defines a “hollow” as “a place or area, especially on the ground, that is lower than the area around it.” In Appalachia, they would call it a “holler.” Of these, there are many within the rivertowns—especially in the five square miles that comprise the modern-day Village of Sleepy Hollow and the adjacent parklands of Pocantico Hills. One could imagine any one of these serving as the location for a hair-raising chase involving a headless horseman.

Sleepy Hollow High School students from the early 1970s recall being told that the darkened glen behind their school, where initiates into the prestigious Key Club were taken blind- folded, was, in fact, the site of the assault. That fits the bill in some ways, since Andre Brook (named after the British Major who was captured nearby with documents from the American traitor Benedict Arnold) runs through it.

“Nope,” said Sara Mascia Ph.D., Executive Director of the Historical Society of Tarrytown and Sleepy Hollow. “That’s not it.”

Betsy Bradley, an Irving expert now with Historic Hudson Valley, reminds us that “so much of this, including the landscape, was Irving’s invention.” At the point in his career when he wrote Legend…, he had spent less than a year in the rivertowns as a teenager. He would not actually settle in his Irvington home, Sunnyside, until 1836. But he was apparently mesmerized by the area and soaked up all its lore. As for Sleepy Hollow, says Bradley, “We tend to think of it as a state of mind.”

Historian Richard Rose is far more certain of the location, as is the Village of Sleepy Hollow’s municipal historian, Henry Steiner. The bridge where the Headless Horseman finally caught up with Ichabod was (but is no more) on the lower portion of the Pocantico River, not far from the Old Dutch Church. “There’s no doubt about it,” Rose maintained. Steiner, in his book, Place Names of Historical Sleepy Hollow and Tarrytown, said Irving’s Sleepy Hollow “applies to the lower Pocantico River Valley as it passes through the modern village of Sleepy Hollow.”

Irving himself provides substantiation for this in the story: “An opening in the trees now cheered [Ichabod] with the hopes that the church-bridge was at hand,” he wrote. “The wavering reflection of a silver star in the bosom of the brook told him that he was not mistaken. He saw the walls of the church dimly glaring under the trees beyond.”

So where, you might ask, is that? 

The Pocantico River, really just a gurgling brook, runs southwestward from the Pocantico Hills (Rockefeller country) into the Hudson, which it meets right near the site of Philipsburgh Manor, the farming, milling and trading center, now a stop on the Historic Hudson Valley tour. The river runs right by the Old Dutch Church, then underneath present-day Broadway or Route 9 and into the mill pond that was the natural beginning of the Pocantico River delta—known in Dutch times as “Slapershaven,” or Sleepers’ Harbor, a place where sailors plying the Hudson could take shelter from the rough seas of the Tappan Zee and catch a few Z’s.

There is a plaque at the site of the Broadway bridge that names it the “Headless Horseman Bridge,” but students of local history dismiss that as a convenient way to tie the big paved bridge to the Old Dutch Church that rises on the knoll above it. The real bridge was upstream, “maybe 200 yards,” Rose estimates. This actual bridge, alas, is no longer there, though there is another well-kept wooden bridge further upstream, connecting sections of Sleepy Hollow cemetery. A walk up the road within the cemetery that borders the river can give visitors a sense of just how spooky it would have been in the dark of night in the early 1780s.

And so there are several Sleepy Hollows—the peaceful body of water derived from the Dutch, the deep ravine through which the Pocantico runs, and the village that bears its name. Perhaps Betsy Bradley had it right: Sleepy Hollow is a state of mind.

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