Posted : October 1, 2021
Our blog is chock full of great ideas for fun things to see and do in York Durham and Headwaters. We are always adding new content and updating old posts, but sometimes you might stumble upon something from our vault. If this article has inspired you to hit the road, be sure to double-check that the featured stops in this post are still welcoming visitors.
Everyone loves a good ghost story. Ontario has a vibrant and ongoing history of hauntings and gruesome happenings from long ago. To this day, there are spirits and spectres which roam the halls of our haunted places, often to the terror of the living witnesses who happen upon them… or the thrill, depending on the constitution of the living witness in question.
This season, we have put together a new experience in York Durham Headwaters: our Spine-Tingling Trail. Venture out into our region to learn all about our spooky stories, and visit the places where the dead exist side by side with the living… if you dare, that is. You never know who—or what—might be lurking behind you within these haunted walls.
936029 Airport Rd., Mulmur
The Museum of Dufferin is a wealth of information on Dufferin County’s history, from its Cornflower Glass exhibit, to its Alexandria Hotel in the main exhibit space, to its fantastic educational programming and entertaining events. Staff at MoD also have a wealth of spooky stories of hauntings, murder and mayhem all around Dufferin. Stopping here will give you all the spine-tingling thrills you are looking for, and if you are adventurous enough, you can even go out into the community and visit some of these spots.
The Ghost of Dr. Frame’s Cabin is one such hair-raising tale. Paranormal events have been recorded in this log cabin, which is located just west of Camilla, as early as 1895. Dr. Robert Frame, known locally as a first-rate physician and the best “bonesetter” in the area, lived with his family in the cabin until the early 1890s, before abandoning it. The cabin remained empty until 1894 when the current property owner began renting it out. But no one would stay in the house very long. Complaints of strange noises coming from the attic to disturb the departing tenants was common. One tenant awoke around 1:00 am to a thunderous knocking on the front door. Assuming it was a workman he was expecting to collect some lumber, the tenant crossed the property to the shed where the goods were kept, and was met with a thunderous knocking on the shed door, and the door opening and closing on its own! Strange entities have also been seen, including an unexplained three-prong light shining through the window, and a ball of fire outside the cabin window. The same tenant who experienced the frightening knocking also had his family’s chairs and beds tossed around the cabin.
This story of Dr. Frame’s cabin takes a gruesome twist when a collection of human bones was found in the home. Was it Dr. Frame collecting these horrific specimens? Was it his son, Thomas, who was also a physician? And what did they want with them? Once the bones were discovered, they were buried in a nearby cemetery, and no hauntings have been reported since. So, the question remains… who was the ghost? Was it one of the Frame men intent on keeping his collection a secret? Or was it one (or several) of the victims of Dr. Frame’s gruesome hobby?
More fascinating and terrifying tales of murder, mayhem, spectres and poltergeists are to be had from the Museum of Dufferin. There is the murder of Harry Strutt in Grand Valley, whose ghost re-enacts his shooting on the stairwell of a house on 4th Concession. There is the ghost of James May, who hanged himself, and who may still haunt the water tower. And there is the Springbrook ghost who once wrought terror upon travelers heading past the skew crossing at Earl’s Hotel. For creepy stories of things that lurk in the shadows, Museum of Dufferin is your one-stop-shop for terrifying and true tales!
Make sure you take a stroll around MoD’s Alexandria Hotel to really get you into the spirit (this time the pun was intended). When this old log cabin was moved from its original location and rebuilt at the museum, it appears that a spirit may have come along with it. Staff and visitors feel like they are being watched when they are inside. Be prepared—you may be the next visitor to catch a glimpse of something moving in the old Alexandria from the corner of your eye.
63 Broadway, Orangeville
Unrequited love is the theme of this next haunted stop on our Spine-Tingling Trail. The Greystones Restaurant and Lounge in Orangeville is home to an anxious ghost of First Nations heritage. If you happen to see her standing by the second-storey window, or feel her benevolent presence, you are not alone in your experience. There are several people who have seen this woman—the infamous ghost of Red Feather.
The distinctive Georgian building, originally Graham’s Tavern, was owned and operated by an Irish-born settler named James Graham. In 1879, when Graham passed, his daughter Ann took over the business along with her husband, Thomas Clegg, who was a reputed ladies’ man. It was rumoured that Red Feather, a young woman from the Native summer settlement on nearby Purple Hill who worked at the tavern, was Clegg’s lover. Soon after Thomas Clegg was drawn away by other… ahem… extramarital romantic pursuits, the lifeless body of Red Feather was found on the premises. Heartbroken, she had taken her own life. Some believe today that her body remains on the property, buried either behind the building, or in the cellar. Some also believe that her spirit remains behind as well, and attribute to her the unexplained noises, gentle opening and closing of doors, and sightings of a woman who fits Red Feather’s description.
If you are thrilled by ghostly tales and paranormal events, you may be happy that Red Feather remains at the Greystones. But there is one who would disagree sharply with you. As it happens, there is another ghost haunting the old tavern who goes by the name of Annie. It is reported that she does not like Red Feather or her unearthly presence. Could Annie be Ann Clegg, wife of the unfaithful Thomas? Well, no wonder!
The second floor of the tavern is inhabited by a spirit named Carl. In fact, it is a particular table that he frequents, and when the Greystones Restaurant was the Greystones Inn under previous ownership, this table was always set for two with a bottle of scotch at the ready just for Carl. This ghost is purported to have shared a conversation with a psychic medium, and informed the medium that he remained at the inn because of a confrontation—but would say no more about the matter. Carl preferred his table to be set just so, and had even gone so far as to set it himself when the previous owners purposely left the table in disarray to see what would happen. He is described by those who see him as a bearded man with a mustache, and though he can be cantankerous, he is a nice guy once you get to know him.
Other spectres that have been seen and felt in the building include a young boy of about eight years old in checkered overalls, and the ghost of the notorious Thomas Clegg himself, who some believe still has an eye for the ladies, even in death. In fact, with such a long history, the building is thought to be inhabited by no less than eight spirits who all have connections to the Greystone Restaurant and Lounge’s past.
87 Broadway, Orangeville
Theatres around the world are frequent hotspots for ghostly activity. From set accidents that have tragically claimed the lives of stage workers to the vivacious personalities of passionate actors who love the stage more than life itself, there is no shortage of stories about haunted opera houses and performance venues. Such is the case with Theatre Orangeville. Today, this thriving full-cycle production company is a pillar of the Town of Orangeville and its surrounding area, offering world-class performances, interactive workshops, and education programs for children, adults and otherly-abled community members… to name just a few of its accolades.
Before it was a theatre, this 140-plus-year-old building was the Orangeville Town Hall. Over the several decades that have passed since it was constructed, the building has seen many people come and go. Some, it turns out, have never left. There are rumours of visitors hearing or seeing strange things inside. And spooky occurrences such as disembodied voices, apparitions, unseen presences and orbs of light have all been reported by visitors and staff of Theatre Orangeville.
So enticing were these reports that a group of paranormal investigators travelled to the theatre to conduct a scientific investigation. They concluded that there are three ghosts at TO—two men and a woman. Interestingly, this latter spirit identified herself as an actress to the investigators. It would seem that a true artist is always ready to perform when called upon.
One member of staff, a technician who worked at the theatre for several years, was locking up one night. He was about to set the alarm when he sensed a movement behind him, and turned to find a woman ascending the staircase beside the elevator. Assuming it was a stray patron, he prepared to inform her that she was heading in the wrong direction from the exit… when she vanished before his eyes. Her apparition is described as non-threatening, but unsettling. Is this the ghost of the actress who will not leave her stage? Or perhaps this ghost is attached to another iteration of the building. After all, besides being a theatre and a town hall, it was also a butcher shop and a coroner’s office.
This same technician recalls another occasion of strange noises in the empty building. While he was doing some repairs in one of the dressing rooms, he heard the sound of footsteps on a ladder that was positioned on the stage. Worried about the safety of whoever was climbing, he ran to the stage to reprimand the culprit… only to discover that there was no culprit to be blamed. At least no living culprit.
Why do the ghosts of Theatre Orangeville remain? Is it some terrible tragedy, forgotten to history, that keeps them trapped here? Do they return to the stage for another opportunity to perform? Or, just like live theatre-goers today, do they simply enjoy taking in a good show? No one knows, but all are welcome at Theatre Orangeville—pulse and flesh optional.
1000 Murray Ross Pkwy, North York
This beloved destination is visited year-round by people eager to learn about life in 1860s rural Ontario. Here, school children come with their classes to try their hand at churning butter, making apple dolls and rendering tallow candles. Historians in period costume explain the history of each building on the grounds in fascinating detail. Excited visitors step back in time and are greeted by farmyard friends and working gardens. But there is more than just history that’s hidden in the walls of this living museum.
What is today Black Creek Pioneer Village was once the Stong family farmstead. In 1816 these hardworking farmers arrived in Upper Canada from Pennsylvania, where they spent long, back-breaking months clearing the land and building their home. The lands belonged to the Stong family right up until 1958, when they were sold and immediately redeveloped into Black Creek Pioneer Village. With original Stong structures still on the property and open to the public—not to mention the Stong family cemetery at the back of the village—it is not hard to imagine that members of this pioneer clan have decided to remain in the place that was theirs for generations.
Shuffling of feet, rapping on the walls, ghostly footsteps and a general feeling of unease are experienced by visitors at different times in these historic buildings. In fact, staff at Black Creek believe they know who is responsible for the activity. Michael Stong, who is known to history as the black sheep of the Stong family, had apparently died in a hunting accident over a century ago. This mischievous spirit is known to play with staff and visitors, causing such hair-raising activity as cranking the antique spinning wheel on the second floor when no one is there, and dragging lightweight furniture around in unoccupied rooms.
If that’s not enough to give you the heebie jeebies, Michael may not be the only Stong ghost to roam the old farmstead. In the cemetery, balls of light have been glimpsed dancing between the tombstones.
The Burwick House, which was moved from its original location in Woodbridge, is another haunted structure at the village. The ghost of a forlorn woman is associated with feelings of gloom, disembodied sounds of sobbing, and a thumping noise that is thought to be a wooden cradle on the second floor. Is the sad woman of the Burwick House mourning the loss of a child? We don’t know for sure, but she has been seen by numerous visitors and staff. One report is from a guest who was on a guided tour. When the guide shone her light into an empty room, she distinctly locked eyes with a woman seated on a sofa. Flustered, the guide looked away, and when she looked back… no one was there.
There are several other reports of hauntings all around Black Creek, and we encourage you to visit and hear them all. But there is one more haunting we’d like to mention, and that is the spirit of the Half Way House Inn’s “Lady in Blue.” Originally located in Scarborough, the Half Way House was on the verge of being demolished after years of neglect and ownership changes. At Black Creek, it has been restored and reimagined as the Half Way House Inn. Perhaps this is why the Lady in Blue has returned to the building, now that the building has been returned to the way she remembered it in life. No one knows who she is, but this lady is seen in the upstairs ballroom and on the balcony of the inn. And it is to her that the ghostly activity which many have experienced here is attributed. Is your spine tingling yet?
55 Hedge Rd., Jackson’s Point
The Overlook Hotel from Stephen King’s horror novel The Shining has its room 217. The Briars Resort and Spa in York Region, Ontario also has its room 217. This is the most famous haunting at this charming luxury resort and spa, and it is not unusual for adventurous guests to request accommodations here in the hopes of catching a night of paranormal happenings. The ghost in this room is said to be that of a heartbroken woman who was jilted by her lover while she was staying here in the early 1900s. So devastated was she that she took her life by jumping from the resort’s watchtower. She is described as having long, dark hair and wearing a white gown. Though she may be grieving, she has remembered her manners, and smiles when she shows herself to guests. Or perhaps she is unaware of her audience, and is simply reliving the moments of happiness she felt in life before her heart was broken. Whatever the case, she is associated with a scent of rosewater. Those who have stayed in the room, as well as Briars staff, have reported phenomena such as a pronounced handprint on a freshly made bed, items being moved around after the room had been locked, and curtains billowing in an unseen breeze.
One more thing to note about this lovelorn ghost: her lover, it is said, was a heavyset, balding man with a beard. This female spectre is particularly fond of disturbing anyone who reminds her of her pain. So, if you are hoping to meet her in the flesh (figuratively, of course), you might consider bringing a friend who matches that description to increase your chances.
If you aren’t able to book room 217 for your stay, or if perhaps you’d prefer to leave the adventure to others, then there is still a wealth of spooky sightings and poltergeist activity around the resort. On arrival, you might be treated to a ghostly visit by an elderly gentleman in a Victorian waistcoat who has been seen pacing the lobby. Or perhaps you might see the lady in the white dress who sits at the old piano there. Walking past the dining room might offer you a glimpse of phantom diners dressed in Victorian clothing, and if you’re near the coach house, you may see the apparition of a long-ago caretaker. These phenomena and more have been reported multiple times, by many different guests and employees.
Spend time in Drinkwaters Lounge and you might detect an unexplained whiff of rose and lavender perfume. Or you might catch a lone piano note late in the night when you are alone, like one employee reported hearing. You might even be acknowledged by a friendly apparition or two. One guest recounted meeting a sweet, elderly gentleman in a top hat and with a moustache when he arrived in the lounge. “What do you want to drink, sir?” the man asked. The guest turned briefly to place his coat on a chair, but when he turned back, the guest found he was alone. He searched for the man, but found nothing. Asking a passing server what had happened to the nice man with the moustache, the server informed him that… there was no such employee who matched that description. What can we say? Some of us love our jobs that much.
We don’t know for sure who these numerous ghosts are that are haunting the Briars Resort and Spa. Perhaps they simply loved the place in life and wished to return in death. We don’t blame them—if you have to spend the rest of eternity somewhere, the Briars is certainly a gorgeous place to do it!
460 Botsford St., Newmarket
Deep in the basement of this historic landmark in Newmarket, there is a chilling tale of long-ago dungeons haunted by the people who were kept prisoner there. Old Town Hall has a fascinating history, and has seen different uses over the course of its existence. But there have been suspicious happenings here that date back to the late 1800s, observed and felt by more than just a few people. Walk into Old Town Hall, and you will likely notice the energy of the place. There is a distinct feeling of being watched for many that may be connected to the basement. At one time, the building was a police station, with prisoner cells maintained below street level.
In 2016, the Georgina Paranormal Society conducted an investigation here, in the basement, to determine if any of the reports they were receiving might be true. Using electromagnetic field detectors, thermal cameras and spirit boxes that use white noise to communicate with the long departed, they attempted to make contact with whoever (or whatever!) was in the building—with great success, as it happens. The Society discovered a man inhabiting Old Town Hall who indicated that he had been wrongfully convicted of a crime. But though he did not realize it was the year 2016, he claimed to be happy residing there. Perhaps the eyes that watch you are not always malevolent, then.
… Or perhaps they are, for the investigation discovered more than one voice that night. With a history so rich, and with many people having come and gone through those historic halls, it is understandable that more than one spirit makes Old Town Hall their home, or simply visits from time to time.
The Town of Newmarket is offering a Ghost of Old Town Hall Tours event, where you will be taken on a guided walk down Historic Main Street and into the Old Town Hall, where you will take part in a live paranormal investigation. If your experience leaves you eager for more spooky sightings, be sure to stop by Newmarket’s Grey Goat Pub and Grill. The former Henry Harrison House, this local eatery operates out of a building that was built in 1865, was once a funeral home, and is rumoured to be the location where the original owner died. Enjoy a meal, and if the wind shifts just right, you may be one of the many who have experienced slamming doors, strange noises in the basement, and the outline of an old lady. Dinner and a show? Only if you’re brave.
2365 Concession Rd 6, Greenwood
This collection of historic buildings and artifacts which preserve Pickering’s heritage also preserve the spirits of a few of its former residents. Step back in time to learn about ghosts in Victorian culture, and hear the haunted stories of the Pickering Museum Village on a guided Haunted Walk. Many of these stories come from eye witnesses, and though these guests do not know one another, their tales often recount the same chilling experiences, only in different buildings around the property. Ghosts, it would seem, are not confined to only one set of walls at the PMV.
One such spirit is known as The Man in the Miller-Cole House. This Victorian-era gentleman has been seen by visitors and staff alike. One year, a group of school children was visiting. A volunteer at the museum who was chaperoning the group recalls one of the children asking about the man who was watching them. “What man?” the volunteer replied. “There is no one here.” But the young student was insistent that there was a man standing by the doorway. Astonishingly, the description the child gave matched what other guests had reported previously. The volunteer had no choice but to conclude that this bewildering presence was no earthly one. Who is The Man in the Miller-Cole House? Is he a benevolent spirit, watching over his home and greeting those who visit? Or is his presence more sinister? No one knows for sure, but perhaps you will be the one to answer that question, should you find yourself witness to this mysterious spectre.
The Collins House is another building on the museum’s property which is inhabited by otherworldly presences—yes, plural! Built in the 1830s, this two-story log cabin is home to a living medicinal garden… as well as several non-living children. These rambunctious creatures keep each other company in death, and even know the names of some of the staff who work at the Pickering Museum Village. How do we know? Recently, a team of trained investigators spent time at the museum, conducting a thorough study of the paranormal activity here using the latest technology. Were the stories true, or just a flight of fancy by imaginative individuals? These paranormal investigators believe the stories are real. They were able to determine, by scanning the cabin with a special radio, that when the living children who visit the museum go home to their beds each night, the spirits of other, long-dead children do indeed continue to make the walls of the Collins House their home.
With so many lives having come and gone through the museum’s buildings—buildings which are now historical artifacts—it is no wonder that a few have stayed behind. Especially since most, if not all, of these buildings were in use during the typhus and cholera epidemics that ravaged the City of Pickering nearly two hundred years ago. Come to the Pickering Museum Village and join the Haunted Walk to hear the spooky tales, and maybe a pair of unseen eyes that just might be watching you from around a corner. If you do happen to catch a glimpse of someone lurking in the shadows, staff encourage you say a cheerful “Hello!” Remember: They are probably as curious about you as you are of them.
279 Queen St., Port Perry
There is no shortage of haunted pubs here in York Durham Headwaters. A local tavern has been the want of residents throughout the ages—from settlers’ times right through to today. After all, a good pint, home-cooked food and a meetup with friends is a timeless favourite. Many of our modern pubs, the cozy and popular eateries we love today, were once family homes, loved in a different capacity. Naturally, some of these once private domains are still home to occupants who are not inclined to leave anytime soon. Jester’s Court in Port Perry is one such establishment. It is so haunted that it has been featured in the book Haunted Ontario, written by famed Canadian author Terry Boyle. The building was originally the home of James Carnegie, one of Port Perry’s most prominent citizens in the early 20th century. It is also known locally as The Murray House, likely for the owners who were previous to Mr. Carnegie
The spirits haunting Jester’s Court are certainly active. Whether they are mischievous or malicious has yet to be determined. However, many witnesses have experienced poltergeist activity including salt shakers being fired across tables, paintings spinning on the walls… and a haunted washroom. It is believed that the ladies’ room is frequented by a mysterious “Lady in Blue,” who has been glimpsed by female patrons for many years now, though sometimes her shenanigans aren’t entirely appreciated by living loo-goers.
This particular area of the pub is difficult to keep warm, with some patrons reporting that it feels like air conditioning is being “blasted” into the room. The door to a certain stall is notorious for sticking, and feels as though an unseen hand is holding it shut. One guest recalls using the stall in question, when all of a sudden, goosebumps flushed up her arm and it felt as though she was no longer alone. Making quick work of her ablutions, this guest unlocked the stall door, only to find that it would not budge. She called out asking to be let out, but no one answered. When she called again, the door opened… to reveal that no one was there.
The taps in the haunted washroom are also turned on and off, though this may be the playful antics of a little girl who has been seen. Typically, she is spotted playing innocently on the stairwell which leads from the main restaurant to the second floor. In March of 2000, the presence of this little girl was felt by several psychics and sensitives who were taking part in a paranormal “Meet and Greet” event. She, too, is sometimes seen in the women’s washroom. Did the two female spirits know each other in life, perhaps?
Then there are disturbing reports of an angry-looking older gentleman peering down at departing diners from the upstairs window—a window to a room that is empty. One report tells of the blinds being raised and lowered, a sight which was viewed from the street looking up. It started with a flicker. Then the blind began moving slowly up and down until at one point, it went all the way up and back down again, seemingly on its own, with no hand guiding it. No earthly hand, that is.
Jester’s Court in Port Perry welcomes one and all for great food, great drinks, and a great atmosphere. And if your timing is just right, you may be treated to even more atmosphere than the owners can guarantee. Hold on to your salt shakers, though—you might find them to be the next target of a mischievous poltergeist!
99 Simcoe St. S., Oshawa
There are many haunted places in Durham. Coming in at number six on the scale of most haunted in this up-and-coming region is the Canadian Automotive Museum, located in the heart of Ontario’s Motor City: Oshawa. This museum was established in 1962 as a community project, and is today home to the world’s most significant collection of Canadian automobiles, as well as memorabilia and artifacts like automobile manuals and photographs. It is also home to a spectre or two—who says ghosts can’t also be car enthusiasts?
Murder and mayhem are featured in the stories of many of the automobiles on display at the Canadian Automotive Museum. Famed horror author Stephen King based two of his novels on cars in the museum’s collection. The 1955 Buick Special hails from the same family as the 1953 Buick Roadmaster in the chilling novel From a Buick 8, which was about a haunted police car. And the 1957 Dodge Regent is the same model of car that was used in novel Christine about a car that could regenerate itself after being destroyed (though staff at the Canadian Automotive Museum will note that the vehicle in the book and film was a 1958 Plymouth Fury, which was fundamentally the exact same car as the Dodge Regent, just with the name and badge changed for the sake of marketing). You don’t need to be a car buff to be titillated by these connections to such an illustrious literary horror heritage.
But it’s not just a novel that brings a haunting to life (no pun intended) where this particular 1957 Dodge Regent is concerned. Two ghosts are drawn to the Canadian Automotive Museum’s Dodge Regent, and have been seen by more than a few witnesses. One spirit is said to be that of a First World War veteran who once worked in the building when it was a car dealership from 1921 to 1931. Perhaps he loved the place where he worked in life so much that he decided to remain indefinitely. After all, car enthusiasts are a passionate bunch. Another spirit hanging around the Dodge Regent is that of a little boy. It is thought that he perished in a house fire in the 1920s, built on the spot where the museum’s parking lot is now located.
The activity at the Canadian Automotive Museum is so frequent that paranormal seekers visit the location regularly, often finding evidence of spirits in the building. The 1965 Amphicar is a particular hotspot, with unexplained orbs seen floating above the car. And the 1912 Rolls-Royce Silver Ghost, which is the rarest vehicle on display at the museum, belonged to Lady Flora Eaton, a cultural icon of early 20th century Toronto, and wife of the heir to the Eaton’s department store dynasty. This stunning vehicle has a hair-raising connection to the supernatural. Interested in the occult, Lady Eaton had a circular séance room built in the turret of her mansion, and had the zodiac painted on the ceiling. When she died in 1970, her maid was so distraught that she hanged herself there. Stand with your back turned to that luxury limousine on a dark and stormy night… if you dare.
But even with all the hauntings and spooky stories connected to display artifacts on the main and upper floors of the Canadian Automotive Museum, the creepiest, most spine-tingling part of the building is the basement. That part of the museum is not open to the public. Count yourself lucky—even those of you brave enough to want to go down there!
York Durham Headwaters would like to credit the following for the stories presented in this article: Pickering Museum Village, Breakfast Television Toronto, Terry Boyle’s Haunted Ontario, Toronto and Ontario Ghosts and Hauntings Research Society, Canadian Automotive Museum, The Durham College Chronicle, The Paranormal Seekers, The Toronto Sun, The Georgina Paranormal Society, The Town of Newmarket, The Regional Municipality of York, Ghosts of Old Town Hall Facebook Group, Museum of Dufferin, The Orangeville Banner, HauntedPlaces.org.”