Around the Island

Haunted Tales of Sylvester Manor

ANNETTE HINKLE PHOTO | Shelter Island's Sylvester Manor
ANNETTE HINKLE PHOTO | Shelter Island’s Sylvester Manor.


She had just started working at Sylvester Manor as a housekeeper, now almost 40 years ago, when Rose Wissemann came in touch with something one afternoon that still haunts her.

She recently recalled that unforgettable day when she had been doing some work in one of the smaller houses on the Manor grounds. As suddenly as a shadow shifts across a floor, an unsettling feeling stole over her. It was a sense that even though she was alone in the place, something — someone? — was with her. She stood still in the room. More than one presence, in some kind of terrible distress, was very near.

Being practical and levelheaded, Rose went about her work and kept the eerie experience to herself.

But a few days later she was passing the time with Eben Case, the master carpenter, who was repairing the staircase in the main house. Rose was saying what a happy house the Manor was and then began to tell Eben about her few disconcerting moments in the other building.

As she spoke, she was struck by Eben’s lack of surprise. He just nodded his head and waited until she was finished before he spoke. Rose was not the first to encounter something otherworldly in that particular building. Eben, whose roots on Shelter Island go back to the 18th century, put down his tools and told Rose a tale of terror, flight and the finding of a safe harbor from torment.

It had long been known, he said, that Quakers who had been driven out of New England by Puritan elders after being beaten, tortured and dispossessed of everything for their beliefs were given shelter by the Sylvester family in that building.

Eben asked Rose how anyone could be surprised if their tormented souls lingered in the place where they had found sanctuary.

The ancient Celts believed during harvest revelries in late October there came one night where only the thinnest of veils separated the world of the living and the dead. Whether one believes this or not, there’s no doubt that everyone loves ghost stories. Rose Wissemann’s story of the Quaker souls is just one of many that has been collected by the staff at Sylvester Manor over the years.

Another tale from the Manor involves a mahogany and gilt mirror dating to the 1750s. It’s said that if you happen to look into the mirror when the light is just right — ideally on a late fall or winter afternoon as darkness finds the corners of the room — a woman in a long white dress will appear in the reflected background. Is this Mary Burroughs Sylvester, another exile, who suffered from mental illness and spent years in treatment, far from the Manor?

No one can say for sure. But historic documents do help round out the tales.

“Every one of our ghost stories actually happened and we know that person existed and has some place in the narrative here,” said Maura Doyle, the manor’s former historic preservation coordinator, during an interview last year. “We do not judge. I myself have never had a paranormal experience, but many other people have.

“What’s fascinating is that there are references to some of these experiences in the family archive that is now at New York University,” she said. “That’s 10,000 documents that include wills, ledgers and correspondence.”

At nearly 400 years old, the Manor has had more than its fair share of history — and ghost stories. Some of the stories can be traced to specific items in the house, like the haunted mirror, while others relate to other parts of the property that visitors can see for themselves.

Along those lines come reports of a female spirit allegedly haunting a section of woods near the Manor House.

“She flits in and out of the trees,” Ms. Doyle said. “The story goes that she was an indentured servant from Ireland. She is seen around there because her toddler drowned in a nearby pond where they used to water the livestock.”

It’s also been said that on certain moonlit nights, a man can be seen rowing a boat silently across Gardiners Creek. More than one person has sworn the man at the oars is headless, a ship’s captain and murderer, doomed forever to row for his sin.

Could it be the infamous and largely misunderstood Captain Kidd or perhaps one of his victims? One tale claims that Kidd, a rumored pirate, murdered two shipmates on the premises who now haunt the grounds.

“Captain Kidd was genuinely involved with Sylvester Manor,” Ms. Doyle said. “He took goods from the Manor to market and would take a consignment fee for doing this.”

ANNETTE HINKLE PHOTO | The indentation in this rock on the Sylvester Manor property is known as the 'Devil's Footprint.'
ANNETTE HINKLE PHOTO | The indentation in this rock on the Sylvester Manor property is known as the ‘Devil’s Footprint.’


Another more mythic tale of the Manor involves the devil himself. The story claims there are three large stones on the East End: one in Orient, another in Montauk and a third at Sylvester Manor. All three stones bear a similar mark or depression that appears to be the “Devil’s Footprint.”

According to legend, God forced the devil out of Long Island and Satan left by taking three giant steps — in Orient, on Shelter Island and finally in Montauk — before disappearing into the ocean. The Journal of American Folklore of 1898 reads: “This footprint is that of a right foot. The impression of the heel and instep is deep and well formed but the toe-prints are lost where the rock slopes suddenly away.” Folklore says that anyone who makes a wish while placing a foot in the footprint for the first time will find it comes true. Do it again, however, and you will receive only calamity for your efforts. It’s also said that horses would not pass the rock without being seized with terror.

“I found out recently that the stone from Orient is now at the Brooklyn Museum. I’d like to find out if that’s true,” said Ms. Doyle. “Ours is still here out by the windmill.”

And who knows what else lurks out there in the darkness, just waiting in the woods of Sylvester Manor?

Happy Halloween!

This Saturday, October 29, “Mysteries of the Manor” takes place from noon to 3 p.m. on the Sylvester Manor grounds. This not-too-scary event will feature kid-friendly haunted hayrides, games and fun fall activities for the whole family. Admission is $5, free for children 5 and under. Costumes are encouraged. Food and beverages will be available for purchase. Rain date will be Sunday, October 30 from noon to 3 p.m. For more information visit or call (631) 749-0626.