“”When things of that nature occur in a small area, people start to think in sort of spooky ways.”
How do you train for a 350 mile winter ultramarathon…when there isn’t snow yet? Some people run. Some drag tires behind them down dirt roads. Some (probably) do very intensive gym regimens. These all sound pretty not-fun to me, and I’m in it for the fun. What’s fun for me is going to the mountains with my pups. So I’m gonna train by going to a mountain with my pups.
The same mountain. Every Weekend. For the rest of the year. It’s one of my favorite spots. I call it ‘the Mountain that made me love Mountains.”
Oh, and the Mountain? It’s haunted.
History and legend(s)
Northeast of Bennington VT, the area around Glastenbury Mountain, at 3,747 feet, covers roughly 36 square miles of unbroken wilderness and includes the ghost towns of Fayville, Glastenbury and the almost-ghost-town of Somerset. It has only six residents. While today Glastenbury is an abandoned wilderness area with mere traces of ruins, a population of nearly 250 people lived in this once-thriving community at its peak in 1880. A series of unfortunate events–economic and natural disasters–led nearly all the residents to move on in the early 20th century. All that remained was an abandoned spot home to a growing list of unexplained phenomena.
The area has long been known for strange events, which led to it’s moniker as the “Bennington Triangle”. The stories about Glatensbury predate its written history–the area was always said to be cursed, according to Native lore. A sampling of the Glastenbury ‘hauntings’:
- An Algonquin legend warned of a malevolent stone in the mountains that would open up and devour anyone unlucky enough to step on it.
- Native tribes also warned of the dangers of this place as the ‘meeting of the winds’, with volatile and unpredictable weather patterns brought on by a malevolent force. They reportedly avoided the area, except to bury their dead.
- Recurring reports have included strange floating lights, other mysterious woodland creatures, and UFO activity. It has been said the town’s graveyard glows at night.
- For more than two centuries, there have been numerous sightings of a bigfoot-like creature in the Glastenbury Mountain area that became known as “The Bennington Monster”.
- People disappear on Glastenbury Mountain. Like…pretty frequently. Frequently enough that it’s a ‘thing’.
Most famously, in 1945, strange disappearances began taking place on Glastenbury Mountain. At least four people in five years have been reported to be hiking on the mountain and were never seen again. Though no direct connections have been found that tie these cases together, other than geographic area and time period, some claim these disappearances were the work of a serial killer. Others blame the Indian curse or the paranormal, stating the place is a “window” into the unexplained. Some say the area is unstable due to wind patterns that are unusually chaotic and confusing, so people can easily get lost. And, predicably, some blamed The Monster.
The only known similarities between the most well-documented cases in the Bennington Triangle are the close proximity of the disappearances, the time of day when most were last seen (between 3 p.m. and 4 p.m.), and the time of year when most were last seen (the final three months of the year).
So…I’m going to go climb Glastenbury, every weekend, for the final 3 [and a half] months of the year! What could possibly go wrong?
Our Own eerie ‘Monster’ Experience
The first time I ever hiked Glastenbury, I did it solo (with Wylie), as a 20 mile, 4,700′ climb day hike. We camped out the night before in the parking lot inside my old Honda Fit (rip, my first adventure friend!) and I used every smidgen of daylight to get the miles in. We completed the last mile with my headlamp on, and I basically had to lift Wylie back into the back hatch he was so pooped. It was a perfect day.
This was fall 2020, when I was noodling the idea of thru-hiking the Long Trail, a 273-mi distance hike that runs the length of Vermont and was the inspiration for the Appalachian Trail. I was also lobbying my little sister, who I refer to online as Auntie, Shelt, and “Art Slut”, depending on the context. I wanted to show her how great it would be, as part of my lobbying campaign. So, a couple weeks after my solo Glastenbury climb, Wylie and I took her back to our recently-discovered spot. We took off for an overnight to camp at a designated shelter site near the summit.
And we had our own spooky Bigfoot experience.
At this time, I knew absolutely nothing about the history and lore of the mountain, or that it is basically the only New England mountain with it’s own Bigfoot legend. So it was a total and eerie coincidence. Prepare for spooky:
It was a dark and not-stormy night. A mild breeze rippled through the towering pine trees blanketing the Goddard Shelter tent site, set on the summit of lonely Glastenbury Mountain. Two women—sisters, in their 30’s—had settled into their tent for the evening with their trusted canine companion. The sisters had enjoyed the waning warmth of the day, sitting in the setting sun’s final sunbeam and handing a flask of bourbon back and forth [notably, one sister had swilled a bit more than the other]. Now, in the pitch black wilderness, they were snuggled tight into to their sleeping bags to stave off the cold bite of the fall night.
Without warning, one sister [the younger] jolted upright, thrashing about wildly. She almost appeared to be looking for something on the floor of the tent. The other sister, and the pup, were alerted awake and struggled to get their bearings.
“Shelt, what the hell? Are you ok?”
“NO! Where is my headlamp…where are my PANTS!?!”
The sister, desperate now, pulled her headlamp on and turned on its bright light. The sisters made eye contact–one seeing the other’s panic in full relief.
“Shelt, WHAT?!”
“I NEED TO PEE! I DRANK TOO MUCH…LIQUID AND I’M GONNA PEE MY PANTS!!”
“I thought you were looking for your pants?”
“I am because I need to…aw, screw it!“
And with that, the younger sister unzipped the tent and flopped out gracelessly onto the dirt. Barefoot, pantsless, she stood up and darted off into the undergrowth of the dense surrounding woods. Only about 12 paces, just far enough to follow social niceties to avoid peeing too proximate to an established tent site (Leave No Trace, people!), before finding relief.
Her elder sister, who for decades has established a firm pattern of never forgetting an embarrassing story and teasing her sister relentlessly, was thereby handed a special gift–a brand new, hilarious anecdote. By the time her wayward companion had made her way back to the tent, The elder had somewhat regained her composure from laughing her ass off and had already dubbed the younger “NakeyLegs BigFoot”, for running through the campsite through the pitch darkness in naught but her undies.
And thus, the legend of NakeyLegs BigFoot was born.
In making good on my lifelong hobby, I of course never let Shelt forget it. I even commissioned a friend, the noted Elkers, to create an original NakeLegs BigFoot drawing–potentially the weirdest commission prompt she’s ever received.
Also, spoiler alert: Shelt, Wylie and I did complete that thru hike a year later, and here’s the pics of us during it climbing the Gastenbury Fire Tower. I’m sure I called her NakeyLegs BigFoot for the entire day.
Let the Residency begin
Did I pick Glastenbury? Did the ghosts of Glastenbury pick me? Who can say. I can make the objective arguments: it simplifies logistics, the repetition eases mental strain on the dogs, the route is fairly low traffic and with no road crossings for the entire mileage, it’s just the right level of difficulty for two ‘lightly past their prime’ dogs while still affording me good training miles…there are good reasons as to why.
But at the end of the day, I have selected to obsessively hike the same mountain, weekend after weekend after weekend, for fifteen straight weekends…and the mountain is haunted.
Let’s see how this goes. Welcome to the Glastenbury Residency. The dogs and I get out there September 13th.
Happy Trails!
For the Nerds
If you want to do a deeper dive, here are some of the sources I pulled from describing the history and lore of the Mountain:
One response to “Welcome to the Glastenbury Residency!”
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[…] dogs and I are five laps into our 2025 Glastenbury Residency. It seems like an apt time to pause and collect my thoughts on our opening salvo into this effort. […]
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