There’s something inherently compelling about secret societies. Are the Illuminati really out there? What goes on at Yale’s Skull and Bones meetings? Is the New World Order truly pulling all our strings? It’s both exciting and scary to imagine there’s something more lurking beneath the everyday trappings of the world.

And yet, answers about the true historical influence of some secret societies might be right in front of those touring one ancient castle in Portugal. Lost in the beautiful architecture are certain details that have folks questioning the architect’s curious associations.

Quinta Da Regaleira in Sintra, Portugal is a wildly popular tourist attraction that is aesthetically beautiful and contains a wealth of secrets. Hidden inside, there’s a history more fascinating than most people truly understand.

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Today, the picturesque patch of land is occupied by a looming and mysterious castle, but the history of the area goes back much further than that. Modern day visitors don’t always grasp the extent of the palace’s legacy.

The area of Sintra that the estate is located on was owned by the Romans from the mid-2nd century BC until years later when a highly peculiar (and somewhat frightening) group took hold of the region.


The group in question was called the Order of Christ, and they considered themselves a successor to the Knights of Templar, an even older organization with a troubled history and bizarre initiation practices.

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The Knights of Templar was a Catholic military order that thrived during the 1100s. In order to join, one was forced to sign over all of his money and possessions, as well as take a life long vow of celibacy and obedience. Fun!

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Then, in the late 16th century, Portugal’s first king — Afonso I — built a castle on the land. Unfortunately, this structure would soon undergo a terrifying and unpredictable fate that left it in utter ruins.

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In 1755 an earthquake swept the region, completely destroying Afonso’s estate. However, this natural disaster had a silver lining, as it paved the way for Carvalho Monteiro, the man who would transform the place into the fascinating enigma it is today.

Monteiro, an entomologist, acquired the land in 1904. He and his architect friend, Luigi Manini, got to work straight away. They had some truly wild plans for the idyllic location.


Monteiro wanted the completed castle to reflect his eccentric interests and hobbies. By the time it was finished six years later, he had definitely succeeded. Quinta Da Regaleira was most certainly a masterpiece.

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Physically, the castle is a combination of Neo-Gothic, Italian Neo-Rennaisance, and Manueline, which is a fancy architectural style that was popular in 16th-century Portugal. However, the messages contained inside are what make the place truly chilling.

This is because Monteiro designed the building to contain many veiled references to different secret societies, including alchemists, Masonry, the Knights Templar, and the Rosicrucians, a 15th-century brotherhood that claimed to have supernatural ancestral knowledge. But it gets odder.


The expansive grounds surrounding the palace have many natural features, including waterways, fountains, grottoes, and gardens. However, out of all these, the most fascinating detail is the initiation well…

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This well isn’t your typical watering hole. It’s huge and ornate, and contains a spiral staircase of nine floors carved into the stone, descending all the way to the bottom. The number of floors included was no coincidence.

The number nine has a special significance in Christianity, representing the completeness of God as well as finality. It is also representative of the eight founding members of the Knights Templar, along with the Grandmaster.


As scary as it sounds, a person would be forced to descend all nine winding flights of the initiation well and travel all the way to the bottom. At this point, they would be made to find their way through a maze of underground tunnels.

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Not even the estate’s chapel is safe from arcane references. Although it’s predominately adorned with typical Roman Catholic decorations, it also includes several pentagrams, a common symbol of the Wicca religion.

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The so-called “Fount of Abundance” is another staple of Quinta Da Regaleira. It’s made from marble and is engraved with elaborate designs, including seashells and strange creatures that resemble snakes. To this day, experts haven’t decoded all the symbols on its surface.

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The symbols and hidden messages dispersed throughout the storied castle are so abundant that many people suspect Monteira himself was a part of one, if not all, of these underground associations. Sometimes the correct answer is the most simple one…


Unfortunately, Monteira himself isn’t around anymore to tell his side of the story. We’ll never know for sure whether or not he really was a member of the societies that so clearly intrigued him.


Quinta Da Regaleira certainly has a past shrouded in mystery, but at least it’s not haunted — as far as we know. The same can’t be said for Leap Castle in Ireland, a chilling historical site that still has experts struggling for an explanation.

Located in Ireland’s County Offaly, Leap Castle draws thousands of visitors every year who come from all around the world to explore its chambers. But, the history it holds is alarmingly morbid.

During the castle tours, visitors meet several people who drop some serious knowledge about the happenings during its heyday. A huge part of what’s imparted on tours points towards the supernatural.

See, there are several ghosts who apparently roam the halls of the castle at all hours. In fact, Leap Castle is so haunted it was featured on an episode of Ghost Hunters.

Historians believe the castle’s been around for about 800 years, but the early beginning is somewhat shrouded in mystery. However, experts think they have a decent idea of what went on centuries ago.

While unsure of who actually built the structure itself, historians have concluded the castle was constructed on a pre-existing site used for ceremonial purposes by the druids. But, this wasn’t what caused the supposed spirits.

Once the druids left and the castle was built, it was originally named Leim Ui Bhanain, which translated to “Leap of the O’Bannons.” The reason behind this unusual name was nothing short of morbid.

The O’Bannons were an affluent clan from Ireland’s County Tipperary, and there were two brothers constantly tussling over who would eventually become chief. In order to decide, they made a bizarre pact.

They would both leap off a high ledge onto a rock below. Whoever survived the impact — or whoever suffered the least injury — would reign supreme. However, the pact never happened.

This was due to the O’Bannon clan getting kicked out of the castle by a more powerful and vicious clan, the O’Carrolls. It was the violence they incurred that supposedly caused the first of the ghostly inhabitants.

Just like the O’Bannons, there were two rival brothers. One was a priest, and in an act of carnage, the second brother murdered him in the middle of mass. It’s said the priest’s spirit now wanders the empty chapel.

Not long after the murder, the O’Carrolls invited another clan, the McMahons, over for a massive feast. But, the O’Carrolls poisoned them all, and now ghosts of several McMahon members aimlessly roam the estate.

The story of the infamous Red Lady involved a woman who was held prisoner by the O’Carrolls. She became pregnant after a sexual assault, and her baby was murdered after birth. The woman then committed suicide, but her specter remained.

Another gruesome feature of the castle is a dungeon beneath a trap door where horrific scenes of torture occurred. Prisoners were tossed down an eight-foot cement hole onto spikes below, where they bled out until death.

Along with the Red Lady, priest, and McMahon clan members, there are also the ghosts of two young girls — Emily and Charlotte — who died during the 1600s. Both have been seen playing together in the Main Hall.

Yet another tale of the paranormal involved the daughter of the reigning O’Carroll chief falling for one of the clan’s prisoners. During an escape attempt, the prisoner killed the heir to the castle, making the daughter the heiress.

She eventually took control of the castle, and along with the ex-prisoner (now a king), began a family. The family amassed riches from battles and hid them in compartments all over. Soon, though, the king spiraled into madness.

After he died, stories of his lonely phantom wandering the castle ground were reported. Some visitors claim they saw him frantically searching for his missing treasure. Eventually, the castle was abandoned completely by the family in the 1920s.

The family fled during the Irish Civil War, and because they were English, the castle was immediately labeled a symbol of oppression. Members of the Irish Republican Army looted and burned the building not long after.

Eventually, an Australian historian named Peter Bartlett purchased Leap Castle in the 70s to restore it. Throughout the process, he claimed he saw many unexplained occurrences. At least the ghosts there leave him mostly alone. He knows how bad haunted homes can get.

Staring up at the gates, lines full of prisoners shuffled in chains into their new home — Eastern State Penitentiary. Opened in 1829, it was a brand new experience for the inmates, guards, and even the warden. This wasn’t your average prison.


Eastern State was the very first official “penitentiary,” invoking a method of rehabilitation that came to be known as the Pennsylvania system: Every aspect of the design of the prison had a purpose that involved paying penance.


The prison itself was famous for its wagon wheel shape called the “hub and spoke plan.” Seven separate corridors, lined with individual cells, pointed towards a center watchtower. In all, it accommodated 450 souls, each in their own mental and literal prisons

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See, each cell was self-sufficient, with a toilet and hot water. A single skylight provided the only light, a representation of the “Eye of God” keeping watch over them, guiding their path to redemption. Even the doors were downsized, so inmates had to physically bow down each time they entered their cells.


In those cells, they were kept in solitary confinement, which was supposed to be revolutionary. It was an experiment with a new emphasis on rehabilitation. The point was to remove all distractions, so the prisoner would seriously reflect on their crimes.


Initially, the inmates fated to the sanity-breaking sentence of solitary confinement were largely first-time offenders. It was a dump for petty criminals — robbers, pickpockets, small-time thieves — who ultimately suffered a punishment worse than rubbing elbows with the worst kinds of criminals.


Over the years, the prisoners outnumbered the cells, so they abandoned the solitary style out of necessity in 1913. Sadly, they still used “the hole” as means of punishment, leading prisoners down a special staircase to the basement where an eerie hall of forgotten cells waited.


The toxicity of the environment was evident early on. Charles Dickens visited and described it as such” “I am persuaded that those who designed this system…do not know what it is they are doing…I hold the slow and daily tampering with the mysteries of the brain to be immeasurably worse than any torture of the body.”


Isolation was just a way to break down the psyches of the inmates. Torture was another popular practice. Punishments included submerging men in freezing water, then leaving them outside in the harsh winters till frost covered their skin.


Another gruesome act included shackling an inmate’s tongue to their wrists. Any attempt at movement would pull at their tongue, risking yanking clean from their mouths if pushed to continue resisting. The prisoners learned that the disorientation of constant isolation was preferred to the hands of the guards.


Of all the high profile names to pass through Eastern State Pen, the worst was mobster Al Capone. His stint was short, just 7 months. During his period of isolation, it’s said Capone would shout in fear “Jimmy!” Either an invisible tormentor or a symptom of later mental decline, no one is sure.


Phantom Jimmy aside, Al Capone was hardly suffering in prison. His cell was decked out. Like other inmates, he was stuck in an 8 x 10 cell, only his came fitted with high-end furniture, oil paintings, and a radio.


Not all the inmates received a cushy welcome, or really deserved to be there at all. Governor of Pennsylvania Gifford Pinchot sentenced a dog to wear prison stripes at Eastern State. His crime? Murder. The victim? Pinchot’s beloved cat Pep. 

Eastern State was officially made a national historic landmark in 1965, small comfort for the prisoners still locked inside. It officially closed in 1971. The prisoners were transferred to nearby institutions. For the first time in over 100 years, the complex was empty.


After 20 years of neglect, the prison reopened. The historic landmark is available for tours 7 days a week with guides or an optional audio component narrated by actor Steve Buscemi. But not every visitor to the prison is there to learn about history…


During its heyday, Eastern State had more than just the lingering negative energy of torture and seclusion. Records indicate over 50 separate suicides took place inside the prison. Prisoners knew there was a high probability of leaving in a body bag.


Inmate-on-inmate violence is a harsh reality for every prison, and Eastern State was no different. There were over two dozen murders documented on file, and in some cases, some prisoners just vanished, with no explainable cause or trace.

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It garnered a reputation within the paranormal investigation community as a hotbed for activity. Ghost Adventures, Ghost Hunters, and Buzzfeed’s Unsolved have filmed lockdowns inside the prison, and it’s always on the shortlist for the most haunted structures in America.

Current and former staff have heard weird sounds, like footsteps in completely vacant sections of the prison. On several occasions, people reported hearing the sharp wails of a baby. All the ghostly suspicions are further fueled by photos of orbs snapped by countless visitors.

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The spirits lingering in Eastern State Pen are known to get physical. Cell doors were witnessed to slam shut without provocation. Others report feeling hands grasp their shoulders, potentially a departed inmate driven to madness, reaching out for human contact.


The place also hosts art exhibits, including one hair-raising series called Ghost Cats. Artist Linda Brenner installed 39 white cat sculptures about the grounds, representing a cat colony that lived on premises in the ’70s. But ghosts are still the main attraction.


Every year, Terror Behind The Walls runs from September through November. It boasts the title of largest haunted attraction in the U.S., making Pennsylvania a hub for paranormal vacations, since Gettysburg is near the top of any ghost enthusiasts’ must-see list.


According to legend, ghosts of the fallen soldiers still roam the empty fields of Pennsylvania’s Gettysburg, a site said to be one of the most haunted places in the world. In 2013, two believers investigated the rumors, and what they found got people talking.

These men heard stories about ghosts at Gettysburg, and a ranger told them at the time that tourists had been spotting apparitions, too. Eyes peeled, they drove down the empty road that ran parallel to one of the enormous battlefields.

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They pulled over beside a pair of cannons and turned off the car—a bad idea if horror movies were anything to go by. With their cameras rolling, they chatted idly, waiting for something—anything—to happen. Initially, they saw no ghosts.

Obviously, the lack of ghostly figures was disappointing. This was Gettysburg, after all, home to one of the bloodiest battles of the American Civil War. Combined, the Union and Confederates suffered about 50,000 casualties. In other words…

If paranormal activity truly existed in the world, this should have been a hotbed for it; ghosts should have been practically strolling down the street, whistling a tune! Yet, after 20 minutes, there was nothing. That was when something caught their eye…

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With a little help from zoom-enhance technology, it was possible to see just what had captured the attention of the two men. Had an apparition really appeared right in front of them? Or were they only seeing a ranger out for a midnight walk?

As the men’s excitement—and panic—rose, the figure stepped out from behind the cannons. Sure enough, it was looking pretty ghostly—it was transparent! Then, rounding the cannons, it turned right for them.

Luckily for these two men, this particular ghost of Gettysburg wasn’t the murderous type. After just a few steps, it disappeared, gone back to the spirit world to haunt and spook another day. Um… what just happened?

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Now, you might be thinking, I’m on to you, clearly, this is a camera or computer trick. After all, with today’s editing technology, even a kid could insert a ghost into a few frames of dark video. This couldn’t be real, right?

Not so fast. A park ranger named Maria Brady relayed a tale to the Washington Post that might suggest there was more going on in the video than camera tricks. Her explanation started with an area called the Devil’s Den in Gettysburg…

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There, Maria had discovered an envelope filled with rocks. Inside the envelope was a letter. According to Maria, it read, “Please return these to Devil’s Den, we are sorry.” Believe it or not, this wasn’t the first time that rock-filled letters were found at Gettysburg!

Gettysburg National Military Park via the Washington Post

See, over the years, another rumor circulated around Gettysburg: the rocks there were cursed. Whoever pocketed a stone and brought it home faced terrible luck—forever. And plenty of park patrons confirmed that ghostly legend.

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For instance, another park visitor sent a letter to Gettysburg (also containing stones he’d regrettably swiped from the park) explaining that his life had since fallen apart. He’d lost his job, his house, and his wife. Oh yeah, and he spent some time in prison.

“That was just the worst list of stuff that happened to somebody that I’ve ever seen,” Maria told the Post. “I mean, a lot of [the letters] are, ‘I broke my arm,’ ‘I lost my job,’ but, you know, when you go to prison for nine years?” Brutal.

As people from all over the county visited the old battlefield, enough left with spooky stories that indicated those ghost hunters’ first encounter might not be so far-fetched. In fact, another viral video from 2009 seemed to corroborate their story…

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After hiking off the main road, just about a mile away from Triangular Field—allegedly the most haunted location in all of Gettysburg—a couple set up a mounted camera at dawn and filmed for three minutes across nine locations.

They were filming at the second location and the sun hadn’t yet peaked over the trees. The ex-battlefield was silent—and seemingly ghost-free. But then something emerged from the trees along the horizon…

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Like the ghost in the first encounter, this one took a few steps towards the camera, too, but the camera operators didn’t seem to notice it. What happened next, however, they couldn’t ignore!

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The original ghost disappeared, only to be replaced by a ghostly deer! Then, another ghost soldier. And another. Soon apparitions flooded the entire field! Ghosts, it seemed, truly did inhabit Gettysburg!

TCBallinger / YouTube