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Sept. 22, 2020

Ep. 2: Connecticut Legends and Lore, Pt. 2

On part 2 of our series, we chat about 4 more legendary locations and people in the CT area worth discussing—the spooky Dudleytown, the unsettling Fairfield Hills State Hospital, the tragic Leatherman, and the just plain weird Headless Horseman of...

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On part 2 of our series, we chat about 4 more legendary locations and people in the CT area worth discussing—the spooky Dudleytown, the unsettling Fairfield Hills State Hospital, the tragic Leatherman, and the just plain weird Headless Horseman of Canton.

Carrie doesn’t understand why half of the Fairfield Hills buildings are still up, while Sean thinks the Horseman is just a ripoff of Sleepy Hollow’s phantom rider.
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Fairfield Hills State Hospital. I promised I’d come back to this one! We’ve been here, and it’s definitely a...unique place. What’s most bizarre about Fairfield Hills is that the property still exists (though the underground tunnels were filled in), and about half of the buildings from what I can see were refurbished and turned into municipal and commercial offices. The other half were just...left there. Literally there are abandoned asylum buildings right next to shiny town buildings. It’s a really strange dichotomy, and I’m not sure why they chose to leave the abandoned buildings up at all. But it’s there, and it’s definitely an interesting look into the past while standing right in the present.

Fairfield Hills was opened in 1931 to help alleviate overcrowding at other state mental hospitals- because I guess when you’re in a time period where you can be sent to an asylum for sassing your husband or being a woman wearing pants or something, they tend to fill up quick. Fairfield Hills was typical of the time in its treatment of the mentally ill, forcing treatments like frontal lobotomies and archaic electroshock therapy onto patients. There were many stories of suicide, “mysterious” deaths, abuse, and cruelty. So, in short, we’re definitely going there on our honeymoon, right Sean?

Thankfully, the hospital was closed by the state in 1995. Since then it’s been used as a settings in films like Sleepers (which means the hospital is just 1 degree from Kevin Bacon) and the old MTV show Fear, which was a short-lived reality-supernatural TV competition show hybrid where contestants were dropped onto the campus- there called St. Agnes’- to spend the night in September 2000. You can still find this episode, #2 of the show, on Youtube in fabulous ripped-from-a-VHS quality! There are also plenty of unauthorized tours of the place available there as well, if you’re interested. It was supposed to be used as a location once more in a film adaptation of The Madman’s Tale circa 2007, but production never got off the ground. Thanks to the feature on Fear it became THE hot local spot for teenagers to trespass on, so much so that in 2014 the Fairfield Hills Authority voted against letting the show Ghost Hunters film in some of the remaining buildings. And speaking of ghost hunting...

Because of its creepy look and use in horror-related media, the asylum has gained a reputation for being haunted in the years after its closing. Though there’s no specific “you can see evil Dr. Thompson in the window of the lobotomy room to this very day!” haunting stories, there are plenty of claims of sounds and specters. From a rather adorably-titled article in a Halloweentime 2017 issue of the Connecticut Post, ‘Where will the ghosts go when Fairfield Hills is torn down?’, several ghost hunting groups said they expect the hauntings to remain, and even warned that “any location like that that has had a traumatic past, it’s going to leave imprints of negative energy.” Though further demolishings and renovations have made way for a proposed civic and cultural center, as of 2018 some of the largest and spookiest buildings still remained behind chain-link fencing and broken glass. It goes without saying- don’t try and sneak into these buildings at night. But as many people work on this campus and locals are encouraged to walk the trails and bring their dogs there...enjoy the scenery, I guess? 

Aside from the eerie vibes you get when on the campus and the weird doubling sensation of standing in a street with speaking-new buildings on the right and a run-down mental hospital on the left, the only real weird story I have about it comes from my own faulty memory. I remember as recently as my college days there was an awesome website that painstakingly recounted the history of Fairfield Hills. Unfortunately a porn ad site is now camped on the domain (which was super fun to open on my work computer!) but it was still available on the Wayback Machine. I don’t know why I remember it this way, but I recall either at this site or another on the subject, the updates stopped abruptly and it was rumored that the webmaster had died mysteriously. Perhaps the story of Fairfield Hills had driven him mad? In any case, the site is defunct, even if all of the buildings aren’t. 

So Sean, I’m assuming that’s not the only creepy location in the Nutmeg State. 


I’m going to share a short little tale as my final contribution today. This is about The Headless Horseman of Canton. 

I gotta say, I’m a slut for a mysterious horse rider with a pumpkin for a head. Though Washington Irving’s story The Legend of Sleepy Hollow is longer and more dense than you probably remember, it has been a favorite since I was a kid, and I’ve always loved the imagery and my proximity to the Tarrytown-area phantom. Less known, however, is the legend of Connecticut’s own torso-tastic equestrian. According to DamnedCT, the earliest account of the story that can be found originates in The Connecticut Quarterly from late summer 1895, in an article about Canton Connecticut by the Honorable William Edgar Simonds. Quote, “During the Revolution, a French paymaster left Hartford for Saratoga, with his stout saddle-bags filled with gold for the payment of the French officers in the American army. He was traced to this tavern for a night’s rest and no further. The inn-keeper always avowed that lie departed safe and sound, but it was probably heavenward, for no evidence of lateral travel was ever found, and a discovery made after the tavern burned down a few years ago tends toward a belief in his murder. This incident endowed the highway with the legend of a ghastly phantom, a headless horseman to be met at night in a neighboring pass where the trees shadow the road so completely that no sunlight penetrates even at midday.” 

In David E. Phillips’ book Legendary Connecticut, it’s stated that the discovery made at the burned tavern was “the bleached bones of a human skeleton, complete--except for the skull!”

[OMG sound effect]

Another book of Connecticut Curiosities, Connecticut Ghost Stories & Legends, discloses a more detailed account by Canton historian Dr. Lawrence S. Carlton. In this version, which is set one night around the time of the Civil War, a traveler making his way along a deserted Canton highway encounters a horseman standing in the shadows. The traveler asks the horseman if he knows how to get to the Hosford Inn and the horseman just silently points, then gets on his horse and rides away to the west. Deuces, man. It’s only after the horseman leaves, does the traveler realize that the person he just met was...headless!!! 

Like, I dunno how you MISS the fact that someone is lacking their whole-ass SKULL, but there you go. 

Since the story began circulating people have claimed to see a horseman riding west away from the tavern. Apparently, “west” is toward Saratoga New York, though I highly doubt people can tell which direction they’re looking at or have the knowledge of which direction Saratoga is FROM this tavern. I mean, if someone even tells me to go “west” to get to the nearest Dunkin’ Donuts my eyes immediately glaze over, but I digress. The flowy-caped horseman is always on a dark phantom stallion with fiery eyes. My main question is, who murdered the horse!? That’s the real crime here. A Hosford-associated public house did exist in the area in the late 1700s, but nowadays at the purported location--around the Canton junction of routes 44 and 202--all that remains is a fish restaurant and a 1750s era cemetery. Maybe you’ll see the horseman there one night, if you decide to take a romantic stroll through the old cemetery after a delicious dinner of Shrimp Scampi and Calamari Caesar Salad. 

There are so many more weird stories I could tell about Connecticut. For a place seen as stereotypically white-bread, it can be pretty dark when you get into its legends and lore. I’m sure some will say a few biggies are being left out--but have no fear, they’re just being saved for deeper dives or specific compilations. 

One thing’s for sure: you’ll never run out of weirdness in this state.