Most of us are familiar with the Headless Horseman of Sleepy Hollow, the monstrous antagonist of Washington Irving's iconic horror story "The Legend of Sleepy Hollow," written in 1820. Less well known is that Connecticut purportedly has its own decapitated equestrian phantom, also known for terrorizing unsuspecting travelers.
Although rather than the ghost of a Hessian soldier who'd had his head shot off during a battle of the American Revolution, the ghost who supposedly travels the dark and lonely highways of Canton is said to have a more tragic origin.
[Soapbox side note: While researching this story, I noticed that more than one website and publication out there have essentially plagiarized the version put forth by David E. Phillips in his wonderful book Legendary Connecticut—including using specific descriptions and lifting exact sentences—without any sort of attribution or mention of the source material. This has also happened with other subjects I've written about. Here on Damned Connecticut, I really try to give my sources credit rather than pretend like I did the original research or just knew the story off the top of my head. If you see an article where I didn't do so or forgot to give proper attribution, please feel free to let me know. Thanks!]
The earliest account of the story that I can find comes from The Connecticut Quarterly of July, August and September 1895, in a piece about the town of Canton written by the Honorable William Edgar Simonds.
In the early days the largest number of houses was near the center of the town and came to be called Canton Center, but the most important highway in the old town of Simsbury, sometime the Albany Turnpike, with the Litchfield Turnpike branching off at "Suffrage" ran from east to west across the southern part of the present town of Canton; on it at "Suffrage" (now Canton Village) was established in 1798, the first post-office in the town of Simsbury; and, as a part of the Litchfleld Turnpike, there was built across the Tunxis (now Farmington) river, the first town bridge in Simsbury, a mile north of the present Collinsville.
This was a famous old highway, enlivened by many a stage-coach drawn by four or six horses, and made musical by the merry winding of the drivers’ horns. At Suffrage, at the forking of the two turnpikes, there stood for more than a century, the famous Hosford Tavern around which hangs a grewsome story. 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 burred 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.
According to Legendary Connecticut, the "discovery" made at the burned-down tavern was "the bleached bones of a human skeleton, complete, except for the skull!" Dun-dun-dahhh!
In Connecticut Ghost Stories and Legends by Thomas D'Agostino and Arlene Nicholson, there's a more detailed account of the story, penned by the late Canton historian, Dr. Lawrence S. Carlton. In Carlton's version, there's also another layer to the story—one night around the time of the Civil War, a weary traveler making his way along a deserted Canton highway encounters a horseman standing in the shadows; when he asks the horseman if he knows how to get to the Hosford Inn, the horseman just silently points, then gets on his horse and rides away to the west. Only after the horseman leaves, does the traveler realize that the person he just met was headless.
Dr. Carlton also puts a few dates to the story, suggesting that the horseman met his "grewsome" demise in 1781, and that the tavern burned down almost a century later, in 1874.
Over the decades, people have claimed to have seen the horseman, always riding west away from the tavern and toward Saratoga aboard a dark spectral stallion with fiery eyes. (At what point his horse was murdered is never really mentioned, but it would have to have been to be a ghost too, right? Danged details!) With a long cape flowing behind, rider and mount quickly disappear into the night, leaving the hapless witnesses shivering in pure terror.
Now how true is the story? Well, according to the Genealogical History, with short sketches and family histories, of the settlers of West Simsbury, now Canton, Conn., by Abiel Owen, 1856, there was certainly a number of settlers named Hosford who lived in the area in the 18th century, including Gen. Ezekiel Hosford, who seemed to be one of the prominent citizens. Also, there apparently was an inn, also.
From the Genealogical History ... now Canton:
LIEUT. DUDLEY CASE. He removed from the old parish to West Simsbury, about the year 1742. He resided on the place known as the Hosford Stand, where he kept public house for a long succession of years.
Hmm ... was this the inn keeper who allegedly did in the French paymaster and buried him in the basement? Case went on to have at least 10 children, although it's not clear exactly how long he operated the tavern or if any of his children subsequently ran it. There also doesn't seem to be any record of a French paymaster, live or dead, with or without a head. Any connection to the legend is just speculation.
The two turnpikes mentioned are now routes 44 and 202, whose junction are still in Canton. The Hosford Tavern isn't there (although there is a Saybrook Fish House). Interestingly, the Dyer Cemetery, which dates back to 1750 and has a connection to the Case family, is just a decapitated head's throw away.
So what do we have? We know there really was an inn associated with Hosford Stand (as the village was known), which apparently did burn down at some point, and that's about it. The rest of the story—including the gold, the discovery of a body that may have been French paymaster and, ultimately, the sighting of the galloping ghost—all just seems to be fabricated ...
You know, until that one dark and chilly night, when you're out alone on the back roads of Canton, and you encounter a headless horseman, riding away to the west, trying to finish his ill-fated journey. Then it may not seem like such a story ...