bite size hauntings: dudleytown, ct

was dudleytown the real life village of the damned or just a crappy place to live?

I know, I know we still have to finish our journey into Bloody Mary, BUT I had one more horrific tale to tell before we dive in.

This one is a little more obscure, and it’s not about a family, but rather, a town experiencing strange paranormal activity.

Now, I will preface this by saying that the story itself is a bit convoluted and was actually pretty difficult to research. There’s a blurring of fantasy and fact that makes it a hard story to tell, but despite the wildness of the tale, the fact remains that there seems to be something strange going on in Dudleytown.

But, I’ll leave it to you to determine if it’s sheer fantasy or if there’s something to the stories.

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dudleytown, ct

In an almost forgotten little corner of western Connecticut, a small village sits abandoned amidst the dark, dark woods. Referred to as a real-life “village of the damned”, Dudleytown, Connecticut has long been rumored to be an epicenter of paranormal activity.

There is not much left of the little town, save for the crumbling remains of a few stone foundations and walls scattered about the area. But, despite what little is left of the village, whatever caused the people of Dudleytown to leave seems to still remain.

Dudleytown, CT.

Those who have been able to walk amongst the ruins of the town reported seeing shadowy figures moving through the trees and disembodied voices calling them towards the woods. Others have felt cold spots or been overwhelmed by feelings of dread, negativity, and terror. Some have reported seeing mysterious lights within the treeline, and others have claimed to have been touched and scratched by unseen hands.

And perhaps the strangest thing of all is that all who have entered have remarked upon the almost deafening silence that seems to linger over the abandoned town.

Now, according to legend, Dudleytown was founded by one of the descendants of Edmund Dudley, the chief financial agent of King Henry VII.

Edmund Dudley’s story is not necessarily notable. He used his role to siphon money from the treasury while King Henry VII was incapacitated towards the end of his life, and when Henry VIII ascended to the throne and uncovered the deception, Dudley unfortunately had to part with his head.

But, Edmund wasn’t the only Dudley whose head would roll.

His son and grandson, John and Gilford Dudley, respectively, would, unfortunately, meet the same fate after a poorly executed attempt to wrench power away from the Tudor line by inserting their cousin and Gilford’s wife, Lady Jane Grey, onto the throne after the death of Henry VIII’s son, Edward.

You might remember from our Bloody Mary story that Lady Jane Grey did manage to be crowned Queen of England after the Dudley family convinced Edward to remove his sisters Mary and Elizabeth from the line of succession in order to keep England under Protestant rule. Unfortunately for Jane, Mary Tudor wasn’t going down without a fight.

Mary, along with her sister, rallied the nobles and people of England and quickly removed Lady Jane from the throne after a brief rule of nine days. Jane and her husband were taken to the Tower of London and eventually executed for treason. Mary ascended to the throne and well, if you’ve been reading along with us, you know how that ended.

But, what does all this have to do with Dudleytown?

Well, according to lore, the Dudley family, who’d betrayed the King and country multiple times, was cursed. Some might say they were cursed with poor decision-making skills, while others would say there was something much darker at work.

Regardless, sometime after the downfall of Lady Jane, one of Dudley’s descendants decided to travel to the New World. Allegedly, it was his third son, Robert Dudley, but for those of you who know your Tudor history, you know that would be quite impossible, as Robert was the close companion and possible lover of Queen Elizabeth I, who never left England.

Now, John Dudley had many children, so this could be a mistake, but the story goes that a Dudley descendant made their way to the New World and eventually settled in Guilford, Connecticut. He would go on to have a son named William, who would have three sons of his own: Gideon, Abiel, and Barzalli.

Sometime in the late 1740s, Gideon and his family had the misfortune of meeting a man named Thomas Griffs, and this seemingly fortuitous encounter would be something the Dudleys would live to regret.

You see, sometime 1738, Griffs had purchased a large parcel of land from Yale College in an area near what is now referred to as Torrington, Connecticut. At the time, it was a solid investment. The area near Torrington was lush with timber used primarily for shipbuilding. And, because he was a boss babe entrepreneur, Griffs started to sell off small parcels of land, and Gideon Dudley was one of his first buyers.

Gideon had dreams of owning his own farm, and Griffs’ offer seemed too good to pass up. But, the land he’d been sold was hardly meant for farming. Dense trees and mountainous terrain blotted out the sun around the parcel of land. The soil was rocky and unfit for growing, but the Dudleys persisted and by 1753, Gideon’s brothers, Abiel and Barzallai, joined him, purchasing land nearby. A few years later, their cousin, Martin Dudley, would buy his own parcel of land near the brothers, and eventually marry Gideon’s daughter.

More families began to settle in the area, but they would trickle out as slowly as they trickled in. Records indicate that the largest number of families who lived in the small area never exceeded twenty-six, even after iron ore was discovered in the mountains and mining became popular in the surrounding communities.

And that was likely because Dudleytown was shockingly isolated. There were no churches, schools, or shops. Townspeople had to travel several miles to buy provisions. But, it was more than just the ruralness of the village; there was a strangeness to the area itself.

Stories indicate the dense woods and tall hills left the town in darkness as early as noon in the wintertime. And even more bizarre, despite being surrounded by nature, the people of Dudleytown could hear nothing from the woods. There were no animals rustling in the brush or insects chirping, just a dead eerie silence…well, except for the owls.

Dudleytown is actually an unofficial name for the area. The actual name for the location of the village is Dark Entry Forest, but the former residents called it Owlsbury because the only thing anyone could ever hear from the woods were the soft hoots of unseen owls.

So, what happened in Dudleytown / Owlsbury that caused the people of the town to abandon their homes? Well, according to local lore, it was the Dudley curse that destroyed anyone connected to the family.

It started in 1763 with Nathaniel Carter. He was planning on relocating his family to upstate New York, and while he was gone, dealing with the final preparations for the move, his wife and child were allegedly murdered by local Native American tribesmen.

There are two versions of how this story ends:

In the first, Carter returns home to find the scalped bodies of his murdered family strewn outside a burning house, only to discover the tribesmen lying in wait for his return. They scalp him and throw the bodies in the fire.

In the second, with nothing left to keep him in Dudleytown, Carter traveled alone to New York, but despite leaving the town, he could not escape the curse.

Nathaniel Carter was murdered upon returning to his new home in New York state.

The second notable victim of the curse was Gershon Hollister in 1792. According to historical records, Hollister died accidentally while building a barn for a fellow local named William Tanner. Officially, Hollister slipped on a beam and fell to his death, but unofficially, there were rumors that Tanner had murdered the builder.

Now, you might be wondering how Tanner had become an alleged murderer overnight, and it was likely because he supposedly began telling people something from the woods was responsible for Hollister’s death.

It’s said that after Hollister’s death Tanner eventually went mad and died. He did manage to live until a hundred and four, so I suppose if it was the curse, it must have been a rather slow descent into madness.

The third notable victim is Sarah Faye-One, third wife of Revolutionary War Hero, General Herman Swift.

In 1804, Sarah was standing outside one evening when she was struck by lightning on the front porch of their home. Allegedly, after discovering her body Swift went in the way of William Tanner and lost his mind. Now some will say Swift lost his mind later in life, but it feels like splitting hairs since finding your third wife dead and burned to a crisp is probably not positive for one’s mental health.

Sarah’s death is hotly debated when it comes to the curse. The Swift family lived on the far outskirts of what could even be considered Dudleytown and while getting struck by lightning was rare, it was not uncommon in a time when there was little knowledge of storm safety.

Now, our next and perhaps the most famous victim of the Dudleytown curse is Mary Cheney, wife of former Presidential Candidate and founder of The New York Tribune, Horace Greeley.

According to legend, Mary Cheney was born in Dudleytown, and carried the curse with her. A week before the 1872 Presidential Election, Mary committed suicide in a brutal manner, leaving her husband and two children distraught and to Greeley losing in a landslide to Ulysses S. Grant and going insane. Greeley died barely a month later.

It’s a pretty intense story, but unfortunately, Mary Cheney never lived in Dudleytown. She grew up several miles south in the town of Litchfield, Connecticut. There was also no gruesome suicide that led to the downfall of her husband’s campaign.

Mary did die prior to the election, but it was due to complications from a respiratory illness. You see, Mary had actually been sick for quite sometime before her death, and after months of watching her suffer, her passing was ultimately a relief for her family.

As for the election, Greeley did lose in a landslide to famous war hero Ulysses S. Grant, and he did spend the last month of his life in a sanitorium, but it wasn’t because of a curse; it was a series of bad political and financial decisions that pretty much wore Greeley down mentally.

Long story short, both Greeley and Grant were Republicans (back when Republicans were basically Democrats), but Greeley felt the Republican Party under Grant had lost its way and had become too corrupt. He and a group of like-minded Republicans splintered off and attempted in an attempt to push Grant out of the primaries, but they failed to cinch the nomination from Grant.

So, what did Greeley do?

Well, he approached the Democrats, who were desperately in need of anyone to run and were happy to back Greeley as their candidate. However, this would prove to be a really bad idea.

To best frame this, imagine for a moment, if Jon Stewart, a well-known media personality who is an openly liberal, philanthropic activist (who also runs a sanctuary for abused animals on his family farm), one day showed up as the Republican candidate. You’d be aghast, and you’d likely assume that he could not be trusted, despite him saying he was doing this for the people.

Here are a few visual examples of how people felt:

Here we have an illustration of Greeley making a deal with a Democrat, as envisioned by Thomas Nast for Harper’s Weekly (1872).

And here is perhaps my favorite, an illustration of Greeley shaking hands with John Wilkes-Booth over Lincoln’s grave (1872). I don’t know what drugs Thomas Nast was on, but he was bringing a wildly dark energy to the party, and Harper’s Weekly was apparently cool with that.

So, you can see why people felt betrayed when Greeley appeared as a Democrat, and months and months of campaigning couldn’t change that. Greeley had given hundreds of speeches, he’d poured a significant amount of his own money into his campaign and even began selling off his stock in the Tribune to keep funding it.

So, by the time his wife died, Greeley was completely burnt out. His debts were piling up, he’d lost control of his paper, and he was the villain of the story no matter how many speeches or interviews he gave. Greeley not only lost the election, and was left with a little more than $2,500 in his account after debts were settled.

Greeley would attempt to return to the Tribune after the election, but it was clear he was struggling to make it through each day. Around mid-November, it became clear to doctors he was suffering from severe anxiety and insomnia. It was agreed that he should take some time at a sanitarium in upstate New York to recover, but within a few weeks of his stay, Greeley passed.

A tragic story, but entirely unrelated to the Dudleytown Curse.

And whatever happened to the Dudleys of Dudleytown?

Well, they left.

Like most people who eventually moved from the area, the Dudley family realized there was no great fortune to be made in the isolated little village. Farming was near impossible, and while there was a period in time when lumber and mining brought prosperity to the town, lumber began to be used less and less in industrialized society and iron ore was not easy to transport down the mountain to local mills in the area.

To put it simply, as the world around Dudleytown moved towards the future, the small village was too isolated to keep up.

However, one of the Dudley brothers decided to tough it out in Dudleytown, and while there are many stories about how the curse drove him to the brink of madness, Abiel Dudley lived a fairly normal life until the end. From what historians can tell, it seems as though Abiel had dementia in his old age and became something of a ward of the town until his passing.

And while perhaps the conversation of a man slipping back and forth through time with dementia might have seemed supernatural at the time, ninety seems like a pretty decent age for a curse to finally take a man.

Now, there is one final alleged victim of the curse, and I’ll admit this is where it actually gets a bit strange.

Dr. William Clarke had been traveling through rural Connecticut when he stumbled upon the quaint village of Dudleytown. Now, at this point, it was nearly abandoned, but Clarke was undeterred. In 1900, he purchased a parcel of land and built a summer home for his family amidst the mostly abandoned town.

The Clarke family summered in Dudleytown for almost two decades without incident, but then in the summer of 1918, Dr. Clarke was summoned away on business. He returned three days later to find his wife hysterical, claiming there were creatures in the woods that had tried night after night to break into the cabin. Shortly after the incident, Dr. Clarke’s wife was institutionalized and eventually committed suicide.

This supposed incident seemingly did not deter Clarke from continuing to visit his home in Dudleytown. In fact, once Clarke remarried a few years later, he commissioned an even larger home to be built in the area and began to invite fellow professionals from New York to visit Dudleytown.

These colleagues of Clarke’s would eventually go in with him to create the Dark Entry Forest Association, a group that is allegedly interested in the preservation of the Dudleytown area and educating people about conservation efforts; however, their primary interest seems to be in keeping people as far away from the abandoned town as possible.

Now, it is true that Dr. Clarke’s first wife committed suicide after being institutionalized in the summer of 1918, but the Clarke family has always been adamant that any mental distress the first Mrs. Clarke suffered was from a chronic illness and not some creatures in the woods.

And while that very well may be the case, some would argue Dr. Clarke’s enthusiasm for preservation is a bit extreme.

You see, the Dark Entry Forest Association is incredibly protective of its land. According to people who have tried to get close to the town in recent years, there are active patrols in the area. Cars parked on the road too close to the abandoned town are quickly ticketed, and the owners are incredibly serious about prosecuting trespassers.

The Dark Entry Forest Association claims this crackdown was in response to too many teenagers being disruptive in the area after the release of the original Blair Witch Project, but it does strike many people as bizarre that a nature preserve that sits adjacent to multiple public parks is off limits to anyone outside of the Association.

Similarly, the Dark Entry Forest Association has put a great deal of time and effort into writing “debunking” pieces to prove there is no validity to any of the local lore, which again, seems like a weird thing for a natural preservation group to engage in.

So, the sad fact is we may never truly know whether Dudleytown is cursed.

(The Warrens seem to think it stands over a portal to hell, but we know they had a flair for chicanery where money was involved.)

But, one thing we know for sure the Dudley family the town was named after has literally zero connection to the Dudleys beheaded for treason during the Tudor era (that was all just a fun bit of folklore).

There is, of course, another local legend of the land being cursed by the Paugussett tribe as an act of retaliation against the ever-encroaching colonizers, but it would seem to this author that if something does lurk in the woods around Dudleytown, it existed long before colonizers walked these shores.

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Despite the blurring of fact and fiction, the question remains—if Dudleytown is part of a conservation effort, why not allow people to hike or even get close to the area? Why the cameras? Why the tight security and round-the-clock patrols even during the daytime?

Is Dudleytown just another abandoned town mired in folklore or is there something there we should all be glad is contained?

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Resources:

The Curse of Dudleytown by American Hauntings Ink

The Dark Secrets of Dudleytown: Unveiling Connecticut’s Cursed Ghost Town by Emma S.

The Dudleytown Curse, Connecticut’s Village of the Damned by The New England Historical Society

The Legend of Dudleytown by Robert Winkler

The Truth About Dudleytown by the Cornwall Historical Society

This Defeated Presidential Candidate, Once the ‘Best-Known Man in America,’ Died in a Sanatorium Less Than a Month After Losing the Election by Greg Daughtrey