If ghost stories are to be believed, then Long Island must be one of the most haunted regions in the country. This fifty mile drive averages about one ghost every two miles. And this isn’t close to a comprehensive list.
Officially the main road is called New York State Route 25A, but it goes by many names … Northern Boulevard, North Hempstead Turnpike, Jericho Turnpike, North Country Road … as it merges for a while with other roads before splitting off and going its own way once more. It’s been a main east west route since the days of native Americans. Each culture which has passed through here has left its ghostly stamp on Long Island.
You’ll have to leave 25A to find many of these places, but I promise, you won’t have to go far.
Some of these sites are open to the public. Some you can go inside, some you have to wander around outside, keeping an eye on the window for ghostly eyes following you. Still others are hard to see. You might have to settle for a peek through the bushes.
But all of them have stories to tell. Stories of their past, of our past, of life on Long Island. Or in this case, life after death.
The ghost of Cedarmere in Roslyn Harbor … William Cullen Bryant’s haunted estate
Our journey begins at Cedarmere in Roslyn Harbor, the country home of William Cullen Bryant, famed nineteenth century poet and journalist. Bryant is usually thought of as a New Englander, but in reality he spent most of his career in New York, and Cedarmere was where he lived out his life. It was originally a Quaker farmhouse, which Bryant added onto as he expanded the estate. Most of the house burned in 1901, but was rebuilt by his descebdebts using similar plans. It stayed in the family till 1931, when in accordance with Bryant’s will it was donated to Nassau County.
Cedarmere’s haunted reputation includes the sighting of a native American, sometimes seen walking across the grounds at dusk, which is fitting considering the strong presence of native Americans on Long Island.
The grounds include a beautiful Victorian style mill house, where a lady in white from that era has been seen, quiet in her solitude. The house itself has reports of doors opened or closed by unseen hands, strange knocks and taps, as well as shadow people and misty forms.
They couldn’t take it with them, so they stayed behind instead at Glen Cove
Glen Cove attracted some of the richest of the rich in the early twentieth century. The biographies of these families usually include stories of brutal treatment of others in order to build such fortunes. So perhaps it’s a heavy conscious which keeps them tied to places where they lived.
Or perhaps it’s the houses themselves, which trapped their former occupants?
Charles Pratt was one of the pioneers in the oil industry, eventually partnering with John D. Rockefeller to form Standard Oil. The riches from that flowed through the family and poured out into Glen Cove for generations. There are still five massive, ornate estates here built for Pratt’s sons, as well as their own cemetery, which is worth a visit just to see the Romanesque mausoleum, complete with a Bridge of Sighs.
The Manor, now Glen Cove Mansion Hotel and Conference Center was built for John Teele Pratt and Ruth Baker Pratt. While Ruth Pratt was still alive, it was used to film scenes for the Hitchcock film North by Northwest, as well as Sabrina with Audrey Hepburn.
The original owners loved the place so much it seems, that they’ve decided to stick around. A man in a dark brown suit, presumed to be John Pratt is often seen in the main hallways. His wife seems to favor the pub, where she’s been known to play the jukebox and to switch the TV to CSI, which seems to be her favorite show.
One could easily spend a day or more wandering Glen Cove’s gold coast architecture. The crown jewel of those houses remaining is often considered to be Winfield Hall, build by Frank W. Woolworth. Made of pink marble, it’s off limits to the public, though you can catch glimpses of it through the trees.
According to Monica Randall, Mr. Woolworth and perhaps a few other members of his family continues to live on at Winfield. The story she documents in Winfield: Living In The Shadows of the Woolworths is quite harrowing, even if at times one wonders where the facts end and her imagination begins.
But anyone who has stood outside that imposing building can attest, there’s something dark about the place.
Colonial era ghosts, the ghost of slavery and a rough rider haunt Oyster Bay
You can go south from Glen Cove back to Northern Boulevard, which Route 25A is known by along this stretch, or you can wind through the labyrinth of roads that lead to Oyster Bay. If you have time, I highly suggest the winding route, which cuts through one of the more wooded areas of Long Island. Houses alternate between the very old and the very opulent. You can spend a lot of time just admiring the gates even.
As you inch closer to Oyster Bay, you’re moving into some of the most historic areas of the island as well. The original border between Dutch control and the British passed through here, which was the brook which passes through Shu Swamp, a county nature preserve well worth wandering. The last port that Captain Kidd stopped at before being taken prisoner was at Oyster Bay, where he came ashore to visit a friend and begin the process of negotiating his surrender.
The village of Oyster Bay is old, quaint and like much of Long Island, has a bit of a New England feel. Raynham Hall stands in the village itself, a snapshot of the colonial era on Long Island. The history of Raynham Hall begins in 1740 when it was purchased by Samuel Townsend, a young shipping magnate, to take advantage of Oyster Bay’s natural harbor. Townsend went on to aid George Washington as one of the leaders of his spy ring on Long Island.
Slavery was a part of life at Raynham Hall, as Townsend not only owned slaves, but benefitted from their labors through his shipping business. He wasn’t an anomaly in colonial Long Island, as it was a standard practice at the time. Though no less horribly or horrifying than what went on in the south. It’s no wonder that so many colonial era structures on Long island are haunted, for that time was full of horrors.
Even the first known Valentine sent in the United States, presented to one of the daughters of the owner who lived at Raynham Hall, found cupid’s arrow missing its mark. Sally Townsend the daughter of Samuel Townsend had caught the eye of a British officer who was lodging at Raynham Hall during the British occupation. It might have gone better, had her father not been working with Washington as a spy, and Sally overheard the British plans, which she relayed to her father.
Since then Sally has been spotted in her room and the older part of the house. A cold spot is regularly felt in her bedroom as well. Newsday reports other sitings, believed to be a servant who once worked here. But there are a number of ghosts in Raynham Hall, and so far nobody has been able to put names to them all.
The best part is Raynham Hall is open to the public and contains many fascinating exhibitions of a non spooky nature.
The road from Oyster Bay back to Route 25A is another gorgeous stretch of scenery, with Oyster Bay to your left. When you reach the end of the water you hang a left and begin climbing Sagamore Hill to Teddy Roosevelt’s house.
To stroll the grounds is free, but the inside is well worth a visit too. Teddy came out to Oyster Bay from New York City for summers since he was a child and at the age of 22 bought the property where he would build his home. He lived out his life here, raised his family and died at Sagamore Hill.
It’s also said that he never left. After his death the house was kept exactly the way it was when he was alive, and even one of his grandchildren wrote of feeling his presence in various rooms. It’s also thought his wife still remains, who lived for some time after Teddy.
Where the road to Oyster Bay meets Route 25A, you find the Memorial Cemetery of St. John. I’ve never heard any ghost stories about the place, but it’s well worth a visit. Much of it is wooded, with trails running through the woodland, punctuated here and there with rather opulent tombstones and mausoleums. It was designed by the same fellow who designed Central Park, and it shows what a cemetery can be when you give the dead a bit of space.
Jealous ghosts of the whaling era in the footsteps of George Washington at Cold Spring Harbor
As you pass from Oyster Bay you begin to leave behind the Gold Coast mansions. They still dot the area, just not as frequently. What you get instead is a trip back into the colonial era, as well as Long Island Sound opening up beside you. Long Island Sound sometimes lies visible to your left the woods grow thicker, and the small towns look much like like they do all over the country, with businesses packed in along the main street. Albeit on the north shore, the businesses tend to be of a pricier caliber, and trendy bars and restaurants are more common.
Route 25A was always the major thoroughfare along the north shore. Following the revolution, Washington made a circuit around Long Island, starting down the south shore, then cutting across and coming back along the north shore, down 25A. After the island was lost to the British in the Battle of Long Island, it avoided major conflicts, though skirmishes were fairly common. There was resistance, but a large percentage of the population were against the revolution. The British Army occupied Long Island, and it’s believed Washington’s jaunt around the island was to rub it in their faces.
Whatever the reason, Washington’s visit left its mark, and no doubt helped many historic buildings survive because of the association. It’s just a question of knowing where to look. Because everywhere you look, the further east you go, the more history you see.
Off to your right you find Muttontown Preserve. Lost in the woods there is the remains of King Zog’s mansion, torn apart by treasure hunters even before the wrecking ball finished the job. At the other end of the woods is Chelsea Manor, where the children’s grandfather could recite his latest poem The Night Before Christmas.
Then you’re in Cold Spring Harbor, immortalized by a Billy Joel album of the same name. I’m not a fan. But if there’s a musical association to me with Cold Spring Harbor, it’s John Lennon, who had a summer home here.
Cold Spring Harbor itself is a throwback to the 19th century, where you can still feel its history as a port for whaling ships. It looks and feels like its been snatched right off the coast of New England, with its narrow main streets, dotted with tiny shops and Victorian houses.
At least one, The Gourmet Whaler has its own ghost, frequently sighted and felt in the basement. But walking the street at night, you can feel more than that looking out at you from darkened windows.
Then there’s the Harbor Mist, once a brothel, now a restaurant and B&B. A deckhand on a whaling ship came back to Cold Spring Harbor early and found his true love working out of one of the rooms here, and shot her and her customer, who have both been seen and heard there in the years since.
I had a curious experience in Cold Spring Harbor. There was a shop there, now gone which I used to visit regularly. There was an elderly woman who worked there, quite distinguished looking, I always found her working in the back of the store and she always waited on me. Her clothes weren’t old fashioned, just traditionally classy.
One day, after not having shopped there for some time, I stopped in. The lady was nowhere in sight, so I asked her replacement about her. She said she knew of no older woman who had worked there.
Some time later, around Christmas I drove past, and happened to glance at the store. There looking out the front window was the woman.
The rich hug the harbor while the colonial ghosts move inland in Huntington Village
It’s a short drive from Cold Spring Harbor to Huntington Village, where you dip down the hill and into the village proper. Long Island Sound is off to the left, through the residential sections. On the western shore of Huntington Bay you find Coindre Hall
Coindre Hall is a 40 room medieval French château built in 1912 for a pharmaceutical baron. On the outside it is gorgeously intact, with the lawn sloping down to the sound, where you find a boat house built in the same style. Later it became a boarding school ran by the Brothers of the Sacred Heart, until it was bought by Suffolk County. It was used by bootleggers during prohibition and one of the ghosts seen walking the halls resembles a gangster from that era, who it is supposed to have met his end in the tunnel that leads from the house to the boathouse.
Other spirits of that era have been seen, looking far more happy and joyous than the gangster.
Across the harbor from Coindre Hall you find the remains of Ferguson’s Castle, built for Juliana Armour Ferguson, the heir to the Armour Hot Dog fortune. It was designed to resemble a medieval, European monastery, and in fact is still referred to as The Monastery. She went as far as to make the rooms resemble monk’s cells, and used the tombstones of children who died in Europe over 300 years ago as decorations, going as far as to make benches from them.
Mrs. Ferguson loved children, as many people who knew her when they were children happily attest. Her own children were a source of sadness and worry, and eventually maddening grief. A daughter’s divorce was a major blow as at the time divorce, particularly in a family such as hers was more than scandalous. Another son died during World War I, and she had a mannequin brought to the dinner table each night, dressed in his clothes.
It’s that which provides the most horrifying specter reported here. When the building was being torn down, people reported seeing her ghostly figure descending the stairs for dinner.
Today all that is left is a gatehouse, a boat dock and the lower entrance, once a tunnel which led up into the house. And lots of memories.
Back down into Huntington Village itself, things get a bit congested. Up at the top of High Street you find the Conklin Farmhouse, surrounded now by the village which grew up around it, finally hemming it in on all sides.
It was built by the Conkin family about 1750, and remained in the family for about 150 years, before being donated to the Huntington Historical Society. During the revolution, David Conklin was imprisoned by the British, leaving his wife to run the farm and raise the children. This task was likely made easier by the family’s slaves, a small detail usually left out of the historic account, and is another reminder of that ancient scar which still haunts Long Island.
People who have lived there for a time reported feeling someone touching them, laying a hand on their shoulder when no one was there. Another spoke of waking to feel something like a small child laying on their head, smothering them. Another said she awoke to the sound of someone calling her, and opened her eyes to find a young girl there, watching her, who quietly disappeared.
Then there’s the museum volunteer who disappeared, and the last place she was seen was in the Conklin Farmhouse. Legend has it that she’s buried in the basement, which is known to have an oppressive chilling mood. But one would think the police have already looked into that lead, and it becomes yet another mysterious body in the basement story.
As you leave the village the colonial past is on full display. Old Burial Hill was once the site of Fort Golgotha, where the British were quartered during the revolution. They used the tombstones to bake their bread, which left the loaves with inscriptions cooked into them. A bit further down is the village green, now mostly forgotten, and along the side a row of colonial era houses, as well as the old armory from the revolution.
A trip to the funny farm and a drink with a ghost in Smithtown
King’s Park Psychiatric Center lies a few short miles north of Rt. 25A in King’s Park. King’s Park was built to house patients from New York City and Long Island, on a farm setting. The idea was a bit of work would be good for them, and it’s said King’s Park was the original “funny farm.”
It grew on a massive scale, and many of the buildings, some quite impressive still stand though most are in ruins. It’s found within Nissequogue River State Park and there are lovely walks along the river. But you’re not here to enjoy the forest or the water. Except perhaps the water treatments?
All the horrors story cliches you hear about insane asylum find their truth in King’s Park. It all happened here, and the adventurous types are always slipping into the buildings and exploring. Some of those tales are terrifying, sounding as though they’ve been torn from the scripts of a thousand horror movies. Those films about asylums likely have King’s Park in mind as well.
One place you shouldn’t miss is the pauper’s field. The landscape is strewn with bodies of the forgotten, buried without markers, living life with madness and ultimately succumbing to it.
Then it’s back to 25A and a short trip till the giant bull signifies you’re entering Smithtown.
If you’re needing a drink or a bite to eat, Katie’s right there on Rt. 25A in Smithtown would be the appropriate spot. A local watering hole since the early twentieth century, it features live music as well, so it can be a busy place.
That doesn’t stop the ghosts. There’s a lot of poltergeist activity here, much of it caught on security cameras even. Invisible hands have saved a person from falling off a ladder, and once punched a biker in the gut, downstairs in the billiard room. The ghosts down there are said to be more menacing than those upstairs.
There’s no shortage of theories on who or what could be haunting Katie’s. It’s been investigated by many of the big name paranormal shows on cable, newspapers, magazines and paranormal societies. Charlie Klein, a bootlegger and bartender who worked here in the twenties is a prime suspect. He killed himself across the street out of fear of being sent to prison, and he was once part owner of the hotel which stood here.
That hotel burned, allegedly taking several people with it, who might also be responsible for the hauntings. Children are sometimes seen and heard, which cold fit with that story as the building has never been a home. Another investigator said it was the ghost of an old man who was a regular here and died on his stool.
Regardless of who it might be, the one thing you shouldn’t count on is the ghost picking up the tab.
Into the Three Villages where the ghosts are very old
Outside of Smithtown Route 25 and 25A splits, with the latter heading northeast. You stay on that. You’re now on North Country Road, and it truly is a country road. This was farmland, before it became residential with a smattering of commercial along the highway.
On your left you’ll see Deepwell Farms, built about 1845 in a Greek Revival fashion. The resident ghost there is a gentleman, with salt and pepper hair, ascot and smoking jacket.
Just off of 25A is St. James Country Store. This was one of the favored areas for the NYC elite to summer in during the early twentieth century, and the ledger from those days reads like a who’s who of film and politics. It’s still an old fashioned country store, despite having distinctly modern items for sale. The floors still creek, the layout is still early twentieth century, they have a candy counter and a little girl ghost, who is known to haunt the staircase that leads to the second floor.
Down Moriches Road you take Cordwood Path and you’re in a loop that curves around and comes back up along the harbor. This is Harbor Road, a swanky area still, which you’ll find out if you park your car along here for any length of time. The police will remind you in a none so gentle fashion. To your right, facing the harbor you see a curiously shaped house, up on a hill, and if it’s at night there will be a light on in the top floor. According to legend, this was Mary Hatchet’s House, where she chopped her father into bits.
In truth it was the home of the mother in law of Stanford White, the noted 19th century architect. Noted for his ability to design grand buildings with a unique American style, he also boasted a notable mustache and an unfortunate sexual drive. The latter led to his demise, shot in the face by the husband of one of his underage, ex lovers. The sad thing is that led to a Hollywood film, and he’s known more for that than his architectural accomplishments.
Mary Hatchet’s house isn’t one of them. He pronounced it the worst design he ever came up with, but in fairness, it was his mother in law’s idea. It rather puts to rest the idea that this could have once been Mary Hatchet’s house, at least in the sense that people think of that phrase.
He lived at Boxwood, an architecturally significant house which stands in the woods just before you reached Cordwood Path. Just prior to that you passed The Carman -White house, a white Victorian built in the 19th century. Stanford White’s wife had purchased it, along with other land in the area, and following his murder she moved from Boxwood to the Carman-White house.
Subsequent tenants of the Carman-White house spoke of listening to two old women talking in the adjoining room, who might have been the original tenants of the house – two spinsters. Footsteps were common, as well as the sound of someone walking upstairs with a cane. An old portrait was found in a closet with a shattered frame, and repairing that seemed to cause the noises to stop. One woman later reported however, that she heard a voice telling her to go upstairs and when she did she found her baby, choking and turning blue. She was able to save it, but had the voice not told her to check on it …
Head back to 25A and before you know it you’re in Stony Brook, one of the Three Villages which include Old Field and the Setaukets. St. James is frequently lumped in as well. You’re now in one of the most haunted areas of Long Island, or anywhere I’ve been to be honest. Nobody can say why, except perhaps these neighborhoods are very old.
Just down 25A you find the Smith-Hawkins house, which was later the home of one of the most prominent artists to come from New York in the 19th century, William Sydney Mount. The occupation of artist could be tough in those days and one of his specialties in his early career was painting portraits of people’s dead relatives prior to burial. Sometimes the process had to be delayed, and Mount had to view the deceased through a coffin with a glass window, to protect him from the smell.
The house has a long history, being built in 1757 as a store, post office and ordinary. It’s also been a tavern and hotel, and was a center for the Setauket spy ring, which served Washington in the Revolution. Hawkins was also a Freemason, and it’s this connection which some believe drew Washington to stop here on his victory lap after the war.
The main ghost here appears to be William Sydney Mount’s sister, named Elizabeth. Mount himself was a firm believer in ghosts, and for a time, spiritualism. He wrote of a number of supernatural experiences in the house. His ghost isn’t seen here, but instead at the bar the Country House Restaurant, just across the field.
The Country House Restaurant was known as the Hadaway House, and Mount was friends with the people who lived here, and he attended seances they held. But the most tragic ghost in the Country House Restaurant is another lady in white, either hung in an upstairs bedroom by the British for fighting against the crown, or downstairs by angry townspeople who believed she was working for the British. She’s an attractive ghost by all accounts and is rather active.
A few blocks away is the Stony Brook Grist Mill, built in 1751 and still in operation. It’s a step back into time. In the lower section is a set of scales which occasionally swing on their own, blown by a mysterious cool breeze.
Upstairs is yet another lady in white, seen on a number of occasions and believed to be a former apprentice here.
Continuing on, in East Setauket you find the Sherwood-Jayne House, which was built in the 1730s. This was a farm for 150 years, and it’s been faithfully restored to the 1800s. Perhaps it’s this attention to detail that holds the spirits here, which include voices from unseen visitors, cold spots and a man in a blue coat, nervously pacing the grounds.
On the way back to Route 25A, don’t miss the East Setauket Village Green. Beautifully preserved, with two churches and graveyards full of beautiful markers, it’s also the site of a Revolutionary War battle.
Visit in the fall and it’s the quintessential Long Island autumn experience. The mill and mill pond is a great walk, the architecture in this area is gothic, Victorian, early Long Island and the place casts its spell on you. There are rumors of a ghost at the barn by the pond, and also the Emma S. Clark Memorial Library, but in truth, the whole village green is hauntingly beautiful.
How to end any journey? Dinner, drinks and devil worshippers!
The pace of life begins to slow down the further east you travel on the north shore. At Mt. Sinai you find the Mt. Sinai Congregational Church, first established in 1789. Seaview Cemetery is adjacent to the church, and is a hauntingly beautiful, quiet spot.
Behind the church is a nature preserve, once known as the Chandler Estate. The buildings here had long fallen into ruin since its prime, in the days the newlywed Marilyn Monroe and Arthur Miller lived there. Once abandoned, the houses in the woods were according to legend, occupied by devil worshippers, before being razed, which gave the woods its name of Satan’s Trails or Devil’s Gate.
Since then it’s kept up its reputation for cult activity and who knows? Perhaps inspired by the legends some Wiccans or others might occasionally use the trails for rituals. But the legends of innocent hikers being taken for sacrifice are quite likely fabrications.
Satan’s Trails does have a reputation for ghosts, including the unfortunate Ms. Monroe. It’s easy to imagine why a spirit would want to live on in an enchanted woods overlooking the sea, and it’s easy to see why the human mind would conjure up ghosts as well here.
But whether there are ghosts are not, it’s a lovely walk.
And that sums up the appeal to a ghostly drive down Route 25A across Long Island. You likely won’t see any ghosts, particularly when driving by in a car. But you get a lot of history, develop an understanding of the area, and if that’s your thing, you are treated to one of the nicest drives anywhere.
Back on the highway it’s a short drive to Rocky Point and DEK’s American Restaurant, where you find the best cheeseburger on Long Island on the menu, a tasty range of libations, as well as the occasional poltergeist and full bodied apparition.
Or if you’ve a mind, and have the time, you can drive out onto the north fork of Long Island and have dinner upscale at the Jamesport Manor Inn. It was originally a family home, growing ever more elaborate as the family’s fortune grew. Along with fortune came tragedy and the family fell from grace, so the house became a restaurant. It burned later in the twentieth century but was rebuilt from detailed plans. A chance encounter with a guest who swore that lighting a certain candle would bring the ghosts back seemed to work, and since then the new building has been as haunted as the old.
This is just a sampling of the ghosts along the north shore of Long Island, the ones that have made it into folklore, and occasionally history. There are ghosts all over this island, befitting its place in American history as one of the oldest continually lived in areas of the country. Millions of people have lived here, many lived tragic lives and have seemingly unfinished stories to tell.
What to wear on weird Long Island
