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The Haunted Crossing at Ingall’s: Where Ten Night Watchmen Met Their Match
“If ghosts were as plentiful in fact as they are in newspaper columns white-robed shapes and people who can be seen through would be almost as numerous as stray cats.”—White Plains Eastern State Journal, April 23, 1887 In the waning months of 1899, the Ontario and Western Railroad had a problem at Ingall’s crossing on its Northern Division near Middletown, New York. Not a problem with tracks or switches or timetables—those could be fixed. This was a problem of a decidedly more spectral nature. They couldn’t keep a night watchman at the post, no matter how desperately they tried. Nine men quit. Then the section boss himself threw in the…
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The Brutal Murder of Emma Brooks
“Brutally murdered for $300 that she carried on her person, Emma Brooks, an eccentric, unmarried woman, about 70 years of age, was found with her head almost severed from her body, lying in a pool of her own blood, in the front room of an old, secluded house in which she lived, two miles from Highland, on the road leading to New Paltz…” Kingston Daily Freeman, July 15, 1909 The summer of 1909 was marked by a crime so brutal it shocked all of Ulster County. On the evening of July 14th, in a ramshackle farmhouse perched along the New Paltz turnpike near Highland, 72-year-old Emma Brooks met a violent…
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When the Jersey Devil Crossed the State Line: The 1909 Spring Valley Bombat
This is the first in a planned series exploring Rockland County’s surprising abundance of mythical beasts and unexplained creatures. From colonial-era monsters to twentieth-century oddities, Sleepy Hollow Country extends its reach westward across the Hudson. Most people who know anything about the Jersey Devil assume the creature keeps to its ancestral stomping grounds in the New Jersey Pine Barrens—that vast, eerie stretch of scrubby pines and cedar swamps that has harbored the legend for more than two centuries. And most of the time, they’d be right. But in January 1909, something strange happened. The Jersey Devil—or whatever it was—went on tour. During the third week of that month, thousands of…
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Unicorns in the Thickets: Van der Donck’s Dubious Account
Adriaen van der Donck’s 1653 book on New Netherland stands as one of the most important sources we have for understanding the Dutch colonial period in what would become Westchester County. A lawyer by training and the first patroon of what is now Yonkers, Van der Donck was no idle dreamer. His descriptions of the region’s geography, its native inhabitants, and its wildlife are generally accurate, well-observed, and still consulted by historians today. Which makes it all the more curious that buried in his otherwise reliable account is a passage about unicorns. The Unicorn Account “I have been frequently told by the Mohawk Indians,” Van der Donck wrote in Description…
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The Ghost of Estherwood
Just a few miles south of Sleepy Hollow—where ghost stories practically grow on trees—you’ll find the Masters School, a private co-ed institution with a knack for blending academics and a dash of the supernatural. Its sprawling 96-acre campus in Dobbs Ferry, NY, is home to Estherwood, a 19th-century Gilded Age mansion built by James Jennings McComb for his second wife, Mary Esther Wood. And while Mary’s been gone for over a century, rumor has it she’s still hanging around, giving us the latest entry in our paranormal playlist: the ghost of Estherwood Mansion. J.J. McComb wasn’t just a man of wealth; he was a man of clever patents—specifically, a cotton-baling…
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The Devil’s Footprints
Sleepy Hollow Country is steeped in folklore, but few tales are as peculiar as the story of the devil’s footprints in the village of Croton-on-Hudson. We stumbled across this geological phenomenon while sifting through newspaper archives for information on the Black Horse Tavern, a notorious Revolutionary War era public house on the bank of the Croton River. Below the headline “The Devil’s Footprints” ran the lede “Mysterious footprints in the solid rock on the east and west banks of the Hudson at Croton have puzzled the scientists, who believe them to have been made by a primeval man before the Stone Age.” We thought we had a pretty good handle…
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The Bewitched Mill of Sing Sing
The tale of the bewitched mill of Sing Sing comes to us down a winding path—from ancient campfires at the now-vanished shad fishing camp at Crawbucky Point, through newspaper archives, to a battered 1922 pamphlet in the Westchester County Historical Society. It’s the kind of story that reveals as much about how folklore travels as it does about witches and mills. First, a quick note on names: the village we now call Ossining was known as Sing Sing until 1901, when locals, weary of being associated with the infamous prison, opted for a different anglicization of the Mohegan ‘Sint Sinck.’ In our tale, Sing Sing refers to the village, not…
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The Fiery Ghosts of Mount Gulian
Here at Sleepy Hollow Country we first learned of the fiery ghosts of Mount Gulian through a series of articles titled “Weird Westchester Tales,” published in Westchester County newspapers in 1956. Reporter E. L. MacKay opened the series with one of our favorite local legends, that of Spook Rock in Sleepy Hollow. MacKay next shared the following eerie tale from further up the Hudson Valley. The Ghosts of Mount Gulian Unveiled While many have claimed to see or hear ghosts, such stories are often dismissed, especially when the witness is alone. But in this case, the spectral figures were witnessed by not just one, but four people—a policeman and three…
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The Ghost of Sybil Harris King
The ghost of Sybil Harris King is reputed to linger around her former mansion which today is part of the Tarrytown House Estate. This corporate retreat center and event venue, located in Tarrytown, New York, has a rich history that dates back to the 19th century. The property is the combination of three Gilded Age estates owned by wealthy families who were drawn to the Hudson River Valley for its scenic beauty and proximity to New York City. It is situated on East Sunnyside Lane, just off South Broadway and not far from Washington Irving’s home, Sunnyside. Of the three original mansions, two remain standing: Uplands of broker James S.…
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Tarrytown Boat Works
Tarrytown Boat Works was part of a vibrant Hudson River working waterfront during the early years of the 20th century. It was one of at least three boat builders on the Tarrytown waterfront over the years, including local powerhouses John O. Brown and Julius Petersen. While traces of any local boat builders are hard to find 100 years later, we dug deep into the archives to piece together this brief history of Tarrytown Boat Works. Sadly, we have not been able to track down any surviving watercraft from this shop. What we know for sure is that the business was incorporated in 1910. The annual report from the New York…





















