Sin Dee NYC’s Guide to the Haunted Hudson

National Gallery of Art, Public domain, via Wikimedia Commons

“A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere…. Certain it is, the place still continues under the sway of some witching power, that holds a spell over the minds of the good people, causing them to walk in a continual reverie. They are given to all kinds of marvelous beliefs, are subject to trances and visions, and frequently see strange sights, and hear music and voices in the air. The whole neighborhood abounds with local tales, haunted spots, and twilight superstitions; stars shoot and meteors glare oftener across the valley than in any other part of the country, and the nightmare, with her whole ninefold, seems to make it the favorite scene of her gambols.”

The Legend of Sleepy Hollow by Washington Irving

Those words by Washington Irving describing Seepy Hollow, the setting of his most well-known tale, have long fascinated readers. Droves of tourists visit the very real village of Sleepy Hollow in search of a spooky, fun time. The village of Sleepy Hollow and its neighbor Tarrytown make the most of their connection to Irving’s tale, especially around Halloween. While haunted hayrides and horror film festivals may be enough to satisfy your average tourist with the taste for the unusual, the more daring travelers with a deeper level of morbid curiosity will want to investigate the various real-life hauntings that are rumored to manifest in Sleepy Hollow.

The truth is that Sleepy Hollow is a particularly phantom plagued area in the Hudson Valley, which itself is known for its paranormal history. Numerous old legends and bizarre modern-day incidents have led the Hudson Valley to be referred to as the “Haunted Hudson.” The infamous ghost ship the Flying Dutchman has been spotted on the Hudson River. In the town of Nyack is the infamous “legally haunted house” named so for its role in a landmark court case that resulted in a ruling that states potential buyer must be told whether a house is haunted or not.

In the city of Poughkeepsie is the Witchcraft District where among the many Victorian houses in the area is the current headquarters of the Church of Satan. The hamlet of Pine Bush is argued to be the “UFO Capital of the World” due to the high number of aerial phenomena witnessed over the years. Still, it is Sleepy Hollow that is the gateway to the Haunted Hudson.

To get a more thorough understanding of the strange history of Sleepy Hollow I turned to Dani Spencer, an educator and local historian. In addition, she is an avid Halloween enthusiast and ghost hunter. She was able to provide keen insight to the macabre history of Sleepy Hollow.

Dani Spencer, “TarryHollowTown” Historian

“When Washington Irving first visited the region in 1798, Sleepy Hollow and the Hudson Valley was already a mysterious place,” explained Spencer. “A good deal of his inspiration comes from the tales passed down verbally by the old soldiers of the Revolutionary War and the old Dutch housewives of the area.”

Many of these superstitions and legends continue to be passed down. There is a timelessness that is prevalent in the region. There are parts of the area that seem to have changed little since Washing Irving wrote his tale of suspense. “The Hudson Valley still remains a largely untouched land by redevelopment,” said Spencer. “That is changing along the waterfront areas, but we still very much have the grand old spooky houses of yesteryear dotting our quaint Hudson Valley towns. The mere fact that they still exist after a few hundred years and have not been torn down is a good recipe for a ghost in itself.”

Spencer herself can attest to the hauntings in Sleepy Hollow as she claims to have experienced the supernatural while living here. “I have been in a few homes ghost hunting that have had a presence in them,” said Spencer. “One EVP (electronic voice phenomenon) I captured during a private ghost hunt at a haunted bed and breakfast told me to help them and come up into the attic. I still get chills when I think about it.”

If you too want to truly experience the chills in Sleepy Hollow, visit these haunted locations and entities, but only if you dare. “If you are susceptible to different energies,” warns Spencer, “you will definitely feel the shift in air when you enter these places.”

Spook Rock

On the eastern side of the Rockefeller State Park near Saw Mill River Parkway is a boulder in which a mysterious woman in white is often heard wailing. The reason for her banshee-like cry has many theories. Irving himself wrote that it was the ghost of a woman who died from exposure during a snowstorm. Others think the ghost is of a jilted lover who committed suicide. Some say that she is the ghost of a colonial girl who jumped to her death to avoid rape by British soldiers.

The most fascinating story involves a Native American legend:

The Celestial Maiden, or Star Girl as she is sometimes known, was a feminine spirit that descended from the sky onto Spook Rock with her heavenly sisters. They danced around the rock and caught the attention of a hunter from a nearby tribe. He fell in love at first sight with the Celestial Maiden. She was smitten with the hunter as well. She ran off with him and had a child. One day the Celestial Maiden’s sisters returned to Spook Rock to dance, and she couldn’t resist the urge to join in. The Celestial Maiden did not realize that time moves differently when she crosses over. What are hours to her, and her celestial kin are years to humans. By the time she returns, her child had died, and her husband had long been gone as well. She wails in memory of her lost mortal family.

A story like this is an indication that Sleepy Hollow’s ghostly reputation did not originate with Dutch colonists and are in fact a continuation of older indigenous beliefs. “The Native Americans were very prevalent in this area and many of them said the Hudson Valley held an unusual energy to it,” said Spencer. “There is definitely something supernatural about The Hudson Valley.”

Tarrytown Music Hall

Jim.henderson, CC BY 4.0, via Wikimedia Commons

Well, we already knew phantoms like to hang around opera houses, so ghosts in a music hall make sense. The Tarrytown Music Hall is 136 years old which means it had more than enough time to attract a sizable number of ghosts. Numerous specters are said to haunt the theater and since it remains as the oldest theater in Westchester County still in use, many more ghosts will certainly continue to join in with the haunted happenings.

The theater has had many paranormal investigations conducted over the years by noted occult researchers. Amateur ghost hunters can also participate as the theater regularly hosts ghost tours every Halloween season. “The Tarrytown Music Hall is a very haunted place and when I did a ghost tour there, I felt a very strong otherworldly presence there as well,” said Spencer.


JamesPFisherIII, CC BY 3.0, via Wikimedia Commons
Sunnyside, Beyond My Ken, CC BY-SA 4.0, via Wikimedia Commons

Washington Irving himself haunts Sunnyside, the estate in which he lived in. The idea that Irving became a ghost is a bit like Bram Stoker turning into a vampire. Although, as a ghost Irving in not as fearsome a villain as his Headless Horseman. Irving is usually seen haunting a tower known as the Pagoda. Other times he is seen with a quill in hand, writing what could be an otherworldly best seller. Paranormal expeditions are promoted in Sunnyside and are immensely popular during the Halloween season.

Armour-Stiner Octagon House

csouza_79, CC BY 2.0, via Wikimedia Commons

This beautiful, domed building is an architectural gem. For haunted house, it seems too pretty with its lush colors and exquisite design. Of note, is a gorgeous room decorated in Egyptian revival style. While you won’t see any reanimated mummies in the Armour-Stiner Octagon House, you may see the ghost of the woman that haunts the third floor.

She is said to be the ghost of young woman who eloped with a boy her family did not approve of. The two lovebirds unfortunately died when their steamboat sank. Her spirit returned home to haunt the Armour-Stiner Octagon House. No one is too certain where her boyfriend’s ghost ended up. Most likely he’s haunting a far less ornate house.

The Old Dutch Church & The Sleepy Hollow Cemetary

Old Dutch Church, Daniel Case, CC BY-SA 3.0, via Wikimedia Commons

When visiting the cemeteries of Sleepy Hollow, Spencer has some advice:
“Every year thousands of people descend on Sleepy Hollow for October and the one place they all head to for a spooky time is The Old Dutch Church and The Sleepy Hollow Cemetery,” said Spencer. “While we absolutely welcome visitors to both, any kind of ghost hunting on these grounds is strictly prohibited. We love Halloween and history here and ghosts, but not ghost hunting on our very sacred grounds.”

The Bronze Lady Statue

The Bronze Lady Statue is attached to the mausoleum of Civil War General Samuel Thomas. Officially the statue is titled “Recuillment, or Grief.” Among the children of Sleepy Hollow, it is feared as The Bronze Lady. Generations of Sleepy Hollow residents have grown up being dared on playgrounds and school yards to venture into Sleepy Hollow Cemetery and approach the cursed statue. She is said to cry if you go near her. Knocking on the mausoleum door will result in you being visited by nightmares in your sleep. And finally, if you sit on her lap, she will cry blood. Many a supposedly brave boy or girl has run home crying before completing the task.

The Grave of Hulda the Witch

Generations of people who grew up in Sleepy Hollow would tell tales of an old hag named Hulda who would cast spells on the townsfolk. As with many bits of folklore, there are elements of truth to the story. There indeed was a woman named Hulda who existed during the colonial time. She had immigrated from Bohemia and settled in Sleepy Hollow. So, Hulda was real, but was she a witch or not? It seems the age-old conflation of witchcraft with folk healing may be to blame for real-life Hulda’s reputation as a witch.

“During the Revolutionary War when Hulda lived in Sleepy Hollow, she would often bring baskets of healing herbs to the doorsteps of her fellow Dutch neighbors who fell ill,” said Spencer. “The people of The Old Dutch Church named her as an outcast and a witch for her strange ways and she lived alone in the woods.”

Despite being ostracized, Hulda never lost her sense of patriotism. She in fact became a martyr to the cause of independence. “When the British came to town, Hulda took up her musket and actually ran towards the battle in a heroic act of pure courage before she was shot by the British and killed,” said Spencer. “Because she was thought to not be of their same faith, she was allowed to be buried in the Old Dutch Church, but with the condition she have no headstone.”

In 2019, her grave was discovered, and a tombstone was erected on it, thus ensuring that her legacy will be honored. “It is so important that Hulda have a headstone because not only was she was not a witch, but she was a hero,” said Spencer. “She saved many lives of the village with her healing herbs and her patriotism was remarkable as she was an elderly woman living alone in the woods…not the first person you would imagine taking out the invading British.”

The Headless Horseman

We finally come to the most well-known ghost of Sleepy Hollow, the Headless Horseman. In Irving’s short story, the ghost is said to haunt the burial grounds at the Old Dutch Church. A modern-day bridge is labeled, “The Headless Horseman Bridge,” but it’s far from the actual location described in the story. The true bridge unfortunately has been destroyed due to neglect over time.

The Headless Horseman Pursuing Ichabod Crane, by John Quidor, 1858

While The Legend of Sleepy Hollow is an original story by Irving, the phantom known as the Headless Horseman had already existed in the imaginations of Sleepy Hollow villagers.

“Tales of this particular horseman actually existed before Irving even came to Sleepy Hollow,” explains Spencer. “He visited in the summer of 1798 to escape a Yellow Fever pandemic in New York City where he lived, and while he was here, he heard many tales of this horseman from the local Dutch wives of the area, and from an old mill worker he uses to sit and listen to tell stories.”

More than just an old wife’s tale, the Headless Horseman does have a historical background. The Headless Horseman is said to be a Hessian who lost his head during the battle of White Plains. There in fact is a written account in the journal of American Major General William Heath concerning a Hessian soldier who had his head obliterated by a cannon during the battle of White Plains. The battle occurred on October 28th, just three days before Halloween. “These were the seeds planted in Irving’s mind that came to fruition years later when he wrote The Legend,” said Spencer. “Irving was enraptured by their tales of ghosts, bloodshed and battles and that inspiration never left him.”

If you visit Sleepy Hollow this Halloween season, whether you see ghosts or not, I hope the inspiration never leaves you. Have a good haunting!

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