This week on the Backwoods Cryptid Road Trip, we pull into Meriden, Connecticut, and climb into the Hanging Hills, a range of ancient volcanic cliffs where a small black dog has been haunting hikers for more than a hundred and thirty years.
He looks like an ordinary stray. Short hair, black coat, moderate size, nothing about him that should stop you in your tracks. But this dog never makes a sound, not even when you watch him bark, and he never leaves a footprint behind him in dust or snow. And the rule that's been passed down since the eighteen hundreds is simple and merciless. See him once for joy, twice for sorrow, and the third time, you don't come down off that mountain.
We trace the legend all the way back to its source, a story called The Black Dog published in The Connecticut Quarterly in the spring of 1898 by geology professor William Harry Chichele Pynchon, grandfather of the novelist Thomas Pynchon. It was printed as fiction, but it broke loose from its pages almost immediately and became something people swear is real.
We walk through the original three-act tale, the doomed winter climb of geologist Herbert Marshall, and the death that the legend later pinned on Pynchon himself, before separating what actually happened from the story that grew up around it.Then we get into the encounters, because that's where this thing lives. A lifelong hiker watching the dog bark in total silence before he vanishes off a bare ledge. A young man named Mike who photographed the dog at Castle Craig in 2004 while his own brother, standing ten feet away, saw nothing at all.
A nighttime sighting on the bridge over the highway. A skeptic named Christina stunned into belief on the trail below the tower. Prints in fresh snow that stop mid-stride, as if the animal that made them simply lifted off the ground. We lay these against the real and sobering history of the cliffs, including the fatal fall of Mark Valenti in 2015 and the woman who fell nearly two hundred feet in 2021, and we ask whether the legend is wrapping itself around a place that was always going to be dangerous, or whether something up there is doing the counting.
Before we leave the state, we take a side road into Connecticut's wider cryptid country, from the Winsted Wildman of 1895 to the silent eight-foot figure that teenager Karl S. watched cross the railroad tracks near Newtown in 1976, to the all-black upright shape a Bethel woman saw chasing thirty deer through her yard in 2022, to the lanky silhouette that stepped off Holbrook Road near Seymour in 2024. Twenty-some credible sightings, a Litchfield County hotspot, and a long traprock ridge that connects all of it.
Whatever the black dog is, the silence, the missing tracks, and the way it's simply there and then isn't, all of it belongs to the same family of things that walk just outside the edge of what we're willing to call real. Climb up to Castle Craig with us, watch your footing on the ridge, and if you see a small black dog on the trail, take a good long look at him. Because that one's your first.
Have you experienced a Bigfoot sighting, Sasquatch encounter, Dogman experience, UFO sighting, or any unexplained cryptid or paranormal event deep in the woods? We want to hear your story.
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Backwoods Bigfoot Stories is a paranormal storytelling podcast featuring real Bigfoot encounters, Sasquatch sightings, Dogman reports, cryptid experiences, and true scary stories from the backwoods.
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