New England Legends

Podcast 466 – The Ghosts and Monsters of Bennington’s Bottomless Cave

In the woods of Bennington, Vermont, sits a cave that’s said to be bottomless, filled with strange creatures on land where ghosts roam.

The Ghosts and Monsters of Bennington’s Bottomless Cave in Vermont

In Episode 466, Jeff Belanger and Ray Auger hike the woods of Mt. Anthony in Bennington, Vermont, searching for Everett cave. The cave is said to run for miles underground. Strange creatures are said to lurk below, and then there’s the ghost the roams the region.

Read the episode transcript.

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CREDITS:
Produced and hosted by: Jeff Belanger and Ray Auger
Edited by: Ray Auger
Theme Music by: John Judd

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The entrance to Everett Cave on Mt. Anthony in Bennington, Vermont.
The entrance to Everett Cave on Mt. Anthony in Bennington, Vermont.
Inside Everett Cave.
Inside Everett Cave.

EPISODE TRANSCRIPT:
*A note on the text: Please forgive punctuation, spelling, and grammar mistakes. Like us, the transcripts ain’t perfect.

[HIKING IN THE WOODS]
RAY: So we’re hiking up Mt. Anthony, in Bennington, Vermont.
JEFF: Yeah, not far from the Bennington Triangle, and all of those mysteries.
RAY: Right, I’ve heard about the man-eating rocks, people disappearing without a trace, and so much more in the Bennington Triangle. I can’t help but ask, Jeff. Why are we here?
JEFF: I get it. Ray, we’re looking for a cave located right on this trail.
RAY: We parked near Fox Hill Road, we’ve only been hiking a short while.
JEFF: Right… and the cave is just ahead.
RAY: Wow! Look at that. Other caves we’ve explored have been found in the sides of rocks and cliffs, but this one opens down into the ground. (BEAT) Yikes… it’s pretty dark down there.
JEFF: It is… and we’re going inside, Ray. They say this cave goes back for miles, that there’s an underground lake with blind fish, we may find snakes with translucent skin, and of course they say this whole region is haunted. We’ve come to Bennington, Vermont, to explore the mysteries of Everett Cave.
[INTRO]
JEFF: I’m Jeff Belanger. Welcome to Episode 466 of the New England Legends podcast.
RAY: And I’m Ray Auger, thanks for joining us on our mission to chronicle every wicked strange legend in New England. We’re always on the hunt for ghosts, monsters, aliens, roadside oddities, and the just plain weird. We can’t do it without you! So please reach out to us anytime through our website with your story idea. We love hearing from you.
JEFF: Our website is also the place to find out about my story tour. I’ve got dates coming up in Conway, New Hampshire, Voluntown, Connecticut, Dartmouth, Mass, Antrim, New Hampshire, Fall River, Mass, Warren, Mass, and a whole lot more.
RAY: We’ll go exploring the mysteries and monsters of Everett Cave right after this word from our sponsor.
SPONSOR
RAY: Okay, Jeff, I admit it, I’m a little freaked out.
JEFF: I get it. Is it because we’re facing some mysterious cave leading down into the deep, dark, earth, where animals, monsters, and demons could be waiting to hurt or kill us?
RAY: Yeah, something like that.
JEFF: We’ve got our flashlights, we’ve got good boots, maybe we should bring some chalk for spelunking.
RAY: Maybe I should wait outside while YOU go in.
JEFF: (LAUGHING)
RAY: So, the land we’re on was once part of Southern Vermont College. The school closed up back in 2019. Before it was the college, this was all part of the Everett Estate… which is why this place is called Everett Cave. Back in 1910, Edward Hamlin Everett purchased 500 acres of land to build his summer mansion here in Bennington. Everett’s first wife, Amy, died after a prolonged illness. It’s believed that the three daughters he had with Amy didn’t care for his second wife, Grace. So there was tension. Grace was younger, and the couple had two more children together. When Everett died in 1929, he left most of his fortune to his wife, Grace, and only ten percent to be split with the rest of his three daughters.
JEFF: Tale as old as time. When wealthy people die, families are going to fight over the money. The very public lawsuits became known as “The Battle of the Bennington Millions,” or my favorite, “The Second Battle of Bennington.”
RAY: In the end, after dragging everyone through the mud in the news and the public, the courts sided with Everett’s first three daughters. They received the bulk of his fortune. The Everett estate slowly faded. Parts of it were a seminary at one point, and then it became a college back in the 1970s.
JEFF: And that’s when things started getting weirder.
RAY: What do you mean?
JEFF: People started seeing ghosts on campus. There were strange sounds, turning doorknobs with no one on the other side of the door, footsteps that spooked both students and security guards. Then there’s the story of the black-hooded monk that wanders the outskirts of campus, including these woods by the cave.
RAY: This used to be a Catholic seminary way back when too. Maybe that could explain the monk?
JEFF: Maybe. Then there’s the story of the bottomless pond nearby. One witness in the 1960s claimed he saw some women chanting by the pond in a language he couldn’t identify. He watched one of the women take off her robe, dive into the pond, but then she never came up.
RAY: That’s a lot for this one area.
JEFF: It is. The former Everett mansion is also believed to be one of the inspirations as the setting for Shirley Jackson’s Hill House book. As the college students shared these strange stories and wandered the campus and surrounding woods, they discovered this cave. And more legends were born. The blind fish, the translucent snakes, and the haunting and monsters that lie inside a cave some believe tunnels through the earth for over four miles where it comes out in North Pownal, Vermont.
RAY: Okay, that’s freaky too. Ghosts, monsters, mysterious disappearances, and a cave that goes miles through it all. Why are we going inside again?
JEFF: To explore this cave. We gotta know. So let’s head back to 1934, and head inside.
[TRANSITION]
RAY: It’s late October of 1934. Franklin Roosevelt is president of the United States, Stanley Wilson is governor of Vermont, “I Saw Stars” by Freddy Martin is the number one song, and America is still trying to claw its way out of the Great Depression.
JEFF: Here in Bennington, talk of this mysteries cave on the former Everett Estate has reached a fever pitch.
RAY: For generations locals have talked about this cave and its great lengths and depths. They’ve whispered about what may be lurking inside.
JEFF: Today, four men from Springfield, Massachusetts, have made their way to the woods of Bennington to get… literally to the bottom… of this mysterious cave.
[HIKING IN WOODS]
RAY: Here they come now toward the mouth of the cave.
[ROPES/CLANKING METAL]
RAY: Okay, the team has ropes, hammers, lanterns, backpacks with food and other supplies. (BEAT) Are we really going in there?
JEFF: We are, Ray. Get ready.
[WALKING ON GRAVEL]
RAY: Okay, we’re making our way into the mouth of the cave.
JEFF: How are you feeling so far, Ray?
RAY: I’m a little nervous, but okay. We’re walking on a bunch of broken rocks here at the entrance. I can see the cave gets smaller up ahead.
JEFF: Yes, it’s not too bad, though. We just need to crouch through this first turn.
[WALKING ON ROCKS]
RAY: Wow! Okay, now we’re in a pretty large chamber. We can all stand up in here. The room is maybe 25 feet deep. (BEAT) So far we haven’t seen any monsters or creepy crawlies.
JEFF: No, not yet. But speaking of crawling… to get deeper into this cave, we’re going to have to crawl through that gap in the far wall.
RAY: Dude… really? In there?!
JEFF: We got this, Ray. Okay, two of the spelunkers are on now on their bellies making their way in. (BEAT) Okay, I’m getting down on my belly too. (GRUNTING)
[CRAWLING THROUGH DIRT AND ROCK]
RAY: This is getting tighter as we crawl further in. I can’t help but think what could happen if this cave collapses.
JEFF: If this cave collapses now, you won’t have to think about anything…
RAY: Great… thanks for that.
JEFF: The further in we go, the tighter this cave is getting.
RAY: I’m really uncomfortable right now. I’m not sure how much further I’m willing to go in a spot this tight.
JEFF: I get it. Maybe it will open up into a cavern or bigger chamber again soon. If we can just shine a … wait.
[CRAWLING STOPS]
JEFF: They’ve stopped up ahead.
[MUMBLING UP AHEAD]
JEFF: What?!
[MUMBLING AGAIN]
JEFF: Oh man.
RAY: What happened?
JEFF: They reached the end. The cave doesn’t go any further. We need to back out.
[GRUNTING AND CRAWLING]
RAY: I’m happy to get out of here. At some point ghosts and monsters became the least of my worries.
[WALKING ON ROCKS FOR A FEW SECONDS]
RAY: Wow. That was crazy. I saw the guys brought a rope to measure the depth. How far back does the cave go?
JEFF: You ready for this?
RAY: Yeah.
JEFF: 150 feet.
RAY: That’s it?!
JEFF: That’s it.
JEFF: A few days later the Brattleboro Reformer newspaper prints an article on the expedition, basically saying how sad it is that outsiders came in to solve the mystery of the cave. Go ahead and read the last paragraph, Ray.
[SHUFFLES PAPER]
RAY: Okay, it says: It is fortunate that the minds of Benningtonians are at last set to rest. They need no longer shun the cave as a place where disaster awaits the unwitting. But at the same time, it is reprehensible that the honor of exploring the cave should have fallen to outsiders. It is discouraging to that in the town where Ethan Allen, Remember Baker, Seth Warner, Robert Cockran, Ira Allen, Thomas Chittenden, and dozens of other fearless Green mountain pioneers gathered for their councils of war there is not now one man who isn’t afraid of the dark. The ghosts of the men who died on the Bennington battlefield shudder at night as they realize that the passes of the Green mountains are now guarded by men whose hearts have softened with their muscles. Ouch!
JEFF: Right?! And that takes us back to today.
[TRANSITION]
JEFF: That article from 1934 is the first mention of the blind fish and snakes with translucent skins inside the cave. I think the newspaper was sad to see the legend shattered—especially by outsiders.
RAY: This is one of the most interesting caves we’ve ever seen while doing this. I mean the earth opens up like a mouth into the darkness below. I’m sure it was easy to wonder what else might be down there.
JEFF: We’ve got many acres of land here that’s seen a lot of history. We’ve got family disputes, a seminary, a college with everything college life brings, and here at the edge of it all, a mysterious cave that sits like a mouth opening up into the underworld below.
[OUTRO]
RAY: And that takes us to After the Legends where we dig deeper into this week’s story and sometimes veer off course.
JEFF: After the Legend is brought to you by our patreon patrons! Thank you patrons for supporting us financially in everything we do. Our patrons help with all of the costs it takes to bring you New England Legends. We don’t work for a big podcast network, we work for you. For just $3 bucks per month you’ll get early ad-free access to new episodes plus bonus episodes and content no one else gets to hear, you’ll get access to our entire archive of shows, and you’re helping to keep this podcast going. To sign up head to patreon.com/newenglandlegends
To see some pictures related to this week’s story, click on the link in our episode description, or go to our website and click on Episode 466.

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We’d like to thank our sponsors, thank you to our patreon patrons, and our theme music is by John Judd.
Until next time remember… the bizarre is closer than you think.

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