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Bennington Horror Story: The Horror of Patch Hollow

What is it about odd and creepy places that lure us in so much? Is it the possibility of seeing something unfathomable? Or perhaps our very own game of “Did the curiosity actually kill the cat?” Or maybe it is because we want to find out why this place feels so appealing, yet terrifying at the same time. The mystery almost feels safer than knowing the truth, yet we go after it anyways. But honestly, who doesn’t like to play a little detective? 

Vermont is particularly famous for its creaky houses, ghost towns, and haunted mountains. The Green Mountains, which encircle our campus, have been known to hold a plethora of secrets and old myths which may or may not have followed us into the 21st century. Some of the more famous stories speak of the Bennington Triangle and the now deserted town of Glastenbury. However, few have ventured into the history of the place perhaps just as ominous and isolated:  Patch Hollow. 

Patch Hollow sits in a deep trench in the Green Mountains, surrounded by the slope of Bear Mountain to the west and Button Hill to the east. Its heart: a green swamp filled with skeletons of dead plants which reach for the skies above them. This densely forested area hides the history of one of the main roads in a populated town in southern Vermont. However, if you look at the Hollow today, you never would’ve guessed that it had been a home to people some 190 years ago. 

So what made it go back to its roots? 

Trigger Warning: Murder

The story dates back to May 11, 1831. One of the settlers of the hollow, Rolon Wheeler (known for his wild passions and devious sexual acts, like sleeping with his wife’s sister), had the community turn on him because of his nature. Some members were so resentful and disgusted by Wheeler that they organized a mob to threaten and taunt him. Wheeler then took it upon himself, fearing for his life, to get a knife and guard the door to his home all night long. 

On the night of May 11th, the angry mob, armed with jugs of rum, headed to Patch Hollow to demand justice for such obscene behavior. When they arrived on the scene, realizing that the door was barred, they climbed the roof and got into the house by creating a hole in it. Three men jumped into Wheeler’s home and started fighting him. Wheeler stabbed one of the mob members and slashed another. The cabin door, now unbarred, allowed a number of others to flood the house and start beating Wheeler. In a moment, someone was killed. Prideful and content with their work, the mob stopped to look at their prize – the now dead Wheeler. However, no… No, it was most certainly not Rolon Wheeler, but one of their very own – Issac Osborne. And worst of all, Wheeler was nowhere to be found. 

The mob, terrified and confused by their kill, looked around the now bloodied cabin for any sight of Wheeler. They quickly realized that Wheeler had escaped by prying off some floorboards from under his bed after wrestling off his clothes while fighting with one of the men. Their horror grew bigger and the hollow felt wilder in that cabin than ever before. The mob panicked and left Osborne in the massacre cabin to be found by Dr. John Fox. 

After escaping the mob, Rolon Wheeler spent the night naked in the woods, playing it safe. Once the dusk had settled on the horizon, he stole a shirt from a clothes rack in another town. Finally, he was caught after trying to flee to his sister’s house in a nearby town. 

Both the mob and Wheeler were prosecuted for their actions. Wheeler was found innocent under the terms of self-defense, while the mob was fined by the judge. Some might argue that they finally got the justice that they so very desired. 

After the massacre of Issac Osborne, something sinister started taking over Patch Hollow. Had it been the murder itself or a sense of something greater looming over them, the settlers abandoned the town shortly after and rendered it vanished. And to this day, no one has tried rebuilding the town. 

Today, Patch Hollow is much quieter, yet none the friendlier. 


Iva Sopta is a first-year student studying political science, journalism, and languages.

Bennington Horror Story Columnist, Investigative Journalist, Copy-Editing Team member, Journalistic Education Team member

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