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Discover the Haunting History of Tarrytown and Sleepy Hollow

Photo courtesy of HVA Press

Relive the tall tales and spine-tingling legends behind the Valley’s most chilling, thrilling locations along the Hudson River.

When it comes to folktales and local lore, the Hudson Valley is legendary.

From Rip Van Winkle in the Catskill Mountains to UFO sightings in Pine Plains, the Valley has more than its fair share of otherworldly locations. Nowhere is this more obvious than Sleepy Hollow and Tarrytown. Thanks to Washington Irving’s “The Legend of Sleepy Hollow,” the Westchester locales have developed quite the reputation for chills and thrills. Around Halloween time, rumors of Headless Horseman sightings surge amid visits to Philipsburg Manor and Irving’s Sunnyside home. Were those sounds just bumps in the night, or could they be the rumbles of the Horseman’s steed on moonlit escapades across the Valley?

With tall tales galore in the region, Chronicles of Tarrytown and Sleepy Hollow by Edgar Mayhew Bacon explores the history and legends that define the Hudson Valley to this day. After its original publish date in 1897, the book was reprinted at least seven times before disappearing from shelves for over a century. Thanks to Warwick’s HVA Press, which grants Hudson Valley readers a sneak peek into the page-turner, it’s readily available once more.

Chronicles begins with a foreword by Hudson Valley storyteller Jonathan Kruk, who observes, “anyone bewitched by the headless horseman and all the spirits surrounding him will find solace when seeking the stories at the source of Tarrytown and Sleepy Hollow.”

Settling Into the Hudson Valley

Following Henry Hudson’s Dutch-funded exploratory voyage in 1609, the first settlers in the New York area were Dutch. In the early 1600s, they planted roots along the Hudson River and built foundations for towns and villages that survive to this day. In the book, Bacon delves into the story of Frederick Philipse, the settler who built Philipsburg Manor in Sleepy Hollow. Then the largest estate in the region, Philipsburg was an agricultural hub just as much as it was a miniature castle and, later, a working grist mill.

“[Philipse] chose for the site of his “Castle” the sloping bank at the head of the bay,” Bacon writes. “It was a sunny spot, reclaimed by the woodman’s axe from the forest. We can picture the new cornfields, backing against the sterile line of pine shadow and guarded by grotesque scarecrows that bravely flaunted cast-off greatcoats of linsey-woolsey and three-cornered beavers, worn with a rakish slant.”

Nowadays, Philipsburg Manor is part of Historic Hudson Valley’s annual Halloween extravaganza. In addition to offering tours throughout the year, the site has played host to The Unsilent Picture, a ghostly short film inspired by Irving’s “The Adventure of the Mysterious Picture.”


Ghosts on the Hudson

While many of the Hudson Valley’s spooky narratives go down on land, one particular tale features the Hudson River front and center. Since Bacon’s heyday, whispers of the Flying Dutchman, the ghostly ship that haunts the local waters, have created more than a few goosebumps across the Valley.

In his chapter on myths and legends, the author recounts a supposed spotting of the ship from nearby shores.

“Late on a moonlight evening, several years ago, as two friends sat on the rocks by Kingsland’s round-tower, at the old quarry, and looked down upon the river, their attention was attracted to a schooner that moved swiftly and silently past the point,” he writes. “While the friends were looking at this inviting craft, she disappeared – vanished as completely as though she had been engulfed in the Tappan Zee, leaving not a single spar to mark the place where she went down.”

The Spirit of Major Andre Survives

Poor Major André.

Otherwise known as Benedict Arnold’s compatriot and fellow spy, André was on his way to deliver West Point plans to the British when he was caught and eventually hanged. The hanging took place at a tree in Tarrytown, which was later split by a violent burst of lightning. Since then, it’s said that André’s ghost continues to haunt the grounds that mark his treachery.

“A few reported that they had seen a formless gray shadow whisk by in the neighborhood of the swamp that lay by the side of the highway, and others declared that the word ‘halt’ had been pronounced in a soldierly tone just before the galloping ceased,” Bacon says. “All agreed that the hoof beats stopped as though the rider had reined in suddenly, and that they were never heard further south than the immense old tulip tree, known as André’s tree, that spread its gaunt, ghost-like arms in the moonlight.”

Want to visit André’s ghostly terrain? While the original tree is no longer standing, a monument dedicated to the major rests in Patriot’s Park on the west side of Route 9 between Sleepy Hollow and Tarrytown.

The Headless Hessian Turned Horseman

Before Washington Irving penned the terrifying persona of the Headless Horseman, chances are he found inspiration in the form of the Headless Hessian, a Revolutionary War character thought to haunt Westchester County. According to Bacon, the Hessian was rumored to be a terror, attacking unsuspecting locals in the early days of the Hudson Valley.

“A few years ago,” Bacon begins, “a sober and careful citizen returning from the distant saloon with a pitcher of beer which he was expecting to drink in the bosom of his family, was dragged upon the bridge by invisible hands, though it was clear moonlight, and flung over the high parapet into the water of the Pocantico, where he swam for some time, being miraculously unable to find the shore, and was at last rescued by his neighbors.”

Today, the Hessian has evolved into the Headless Horseman, the blood-curdling character that terrifies readers of “The Legend of Sleepy Hollow” and spooks visitors of Headless Horseman Hayrides & Haunted Houses in Ulster Park.

Want to learn more about the legends and lifestyles of the Hudson Valley during the 1600s to 1800s? Visit HVA Press to read up on Chronicles of Tarrytown and Sleepy Hollow and find a bookstore that carries it near you. If you’re in the Sleepy Hollow region, don’t pass up a trip to Sleepy Hollow Cemetery, where the author himself is buried.

Related: These Are the Most Haunted Cemeteries, Hotels, and Restaurants in the Hudson Valley