The Nefarious Black Horse Tavern

“My way led through a lovely country, rich in charming scenery, and affording far-off glimpses of lordly river and frowning mountains. A picturesque point on the road, going north from Sing Sing, is just before the old tavern is reached…Here the thoroughfare takes a sweep of almost half a circle and crosses the stream over a bridge of rustic character. Black Horse Tavern is a two-story wooden structure, sadly the worse for wear…”

Rambles in Colonial Byways, by Rufus Rockwell Wilson, 1901.

Don’t let this romantic description of the scene deceive you. While the region of Croton is truthfully a beautiful part of Sleepy Hollow Country, the aptly named Black Horse Tavern was not always such a saccharine locale. For much of its long history, it was infamous for its rowdy clientele and grim happenings; known as a “Revolutionary War hangout of muggers and thieves”. This now quaint and nostalgic building has a dark past.

Imagine you are a lone traveler, heading south to the city from Albany with business. It takes about three days to make the journey and you’re close, but the day is getting long. You aren’t on a set schedule, and no one is expecting you, but the sooner you arrive and take care of business, the sooner you can turn back and make the return trip home. It’s unfamiliar territory, but the landscape is beautiful. As your horse walks along, you focus on finding a place to stop for the night before the last day of travel.

Sinister History of the Black Horse Tavern

The Black Horse Tavern sits along the Old Albany Post Road and was one of many stops for travelers and stagecoaches in the 18th and 19th centuries. According to an article from The Highland Democrat in 1915: “This section of the road was in existence before 1750, but not as a through route. There is mention of it as far back as the French and Indian War. The well-known Black Horse Tavern, a short distance south of High Bridge, derived its name from having been the headquarters for the Black Horse Dragoons of that period.”

It is sited just south of Croton-on-Hudson, not far from Van Cortlandt Manor, but a distance from Sing-Sing and Sparta. In the map above, it would be located somewhere near the “C” for Croton Bridge on the west side of the road. The map has errors, so it’s hard to pinpoint a precise location.

Reminiscences of Ossining by Florence Leary Reynolds describes the tavern as sitting “…On a high and steep bank sloping down to the Croton River…two miles or so to the north on the south side of the Croton River, where the stages it by ferry, to the old Ferry House.” That ferry house was near the “Courtlandt Mill” which is labeled on the map.

In the growing dusk, you come upon a dark and hulking structure, windows flickering and illuminated in the gloaming, precariously perched above the steep and treacherous slopes of the swirling waters of the river below. A large wooden sign hangs outside, and the large and black shape of a horse decorates it. Of all the inns and taverns you’d seen and taken advantage of, this wasn’t perhaps the most welcoming looking of inns, but with nightfall quickly approaching, it was safer to stable your horse and take a meal and a bed inside than risk the dangers of traveling the road at night. So you alight from your horse, grab your belongings, and prepare to head inside.

Rufus Rockwell Wilson’s description from 1901 describes the appearance of the Black Horse Tavern as “…a two-story wooden structure, sadly the worse for wear, with a double piazza running the whole length of the front, in the style popular with the builders of country inns a hundred years ago. A wide hall extends from the front door to the kitchen in the rear, and the doors open from it to the sitting room on the right side and the barroom opposite.”

According to local legend, as retold by Reynolds, “sinister tales are told about this tavern”. In the time of stagecoaches and long before telegraphs, when news traveled the fastest by horse, the Black Horse Tavern (sometimes also known as the Black Horse Inn) was a frequented stop for weary travelers to rest. It is said that at one time in its history, a slide-like elevator shaft extended from the back of the tavern to the Croton…”

Your horse secured, and a decent meal in your belly, you sit tiredly near a large fireplace in the Black Horse Tavern’s sitting room and slowly drink a vinegary cider. Across a hall, the bar room is hazy with smoke and thick with the stink of liquor and the patrons. You had carefully threaded through the bodies to procure the cider, but you could feel the eyes of some of them on you. A hand certainly had brushed your pocket. Were they noticing the buttons on your coat? Did they recognize you as not from around here? One of them had commented about the quality of your horse. Something didn’t seem quite right about the clientele, but it was too late to consider getting back on the road. Every so often one of them would turn to look at you from across the hall, dark and with greedy eyes. Perhaps it’s best to head upstairs to bed before things could take a turn.

These “sinister tales” as mentioned by Leary, suggest that the proprietor of the Black Horse Tavern and or local bandits, muggers, and thieves affiliated with the place, would use the rooms of the Inn to rob and then brutally murder solitary travelers. Needing a quick and easy way to get rid of the bodies, the aforementioned “slide-like elevator shaft” now came into play. This chute would swiftly send the corpses of those poor murdered souls away from the inn and into the river, never to be heard from again.

“In those days when news traveled no faster than a horse’s feet…disappearances were difficult to trace, and bodies floated out in time into the Hudson and if found at all might easily be taken as the result of accidental drowning.”

Reminiscences of Ossining by Florence Leary Reynolds

How many possibly met their fates at the Black Horse Tavern, is impossible to say. But the stories circulated for years, suggesting that it was a regular gruesome occurrence, known by everyone but little to be done about it.

In the years following the Revolution and the advent of technology, it would seem that the murderous and deathly connections around the tavern continued to swirl if perhaps the infamous ‘body chute’ was no longer in use.

On August 16th, 1853, a young convict named James Dunn from Sing Sing Prison just to the south had escaped in an ‘ingenious and skillful manner”. A massive manhunt ensued that focused on all the taverns and alehouses in the area, with the searching guards and keepers inspecting the alcohol and bar at each stop. Word reached the searchers that Dunn had made his way to the Black Horse Tavern, the notorious criminal hangout, and off they went to apprehend their man, but also inspect the bar there as well.

Having made a thorough search of man and beverage, the manhunt moved on and became ever more intoxicated as they went, failing in capturing the young escapee and resulting in a large bill to the prison for liquor, of which $25.00 was due to the Black Horse. That’s about a $1,000 tab today.

Later that year in 1853, Mrs. Phoebe Frost was killed in a tragic accident in the area of the Black Horse Tavern. Her horse, attached to her buggy, was spooked and backed itself over the 50-foot precipice above the Croton River, dragging her along with it. Her companion, a Miss Teller, was able to jump off before the fall, but tragically horse and owner were dashed at the bottom of the cliff.

At the turn of the 20th century, the Black Horse Tavern started to experience its inevitable decline. Wilson in 1901, explains that:

“The tavern’s present owner is a pleasant-voiced spinster, who was born there, and remembers well when the stages used to roll up to the door and hungry guests came noisily trooping into the dining-room to partake of her father’s hearty fare. The tavern, in those days, was a favorite meeting-place for the residents of the countryside and the scene of many spirited political gatherings. But with the disappearance of the stage-coaches it ceased to have communication with the outer world, and now there is little of the inn about the old house, while the grass is growing in the road before its door.”

The Black Horse Tavern Today

As the 19th century waned, so did the nefarious goings-on about the place and any stories about the place. In the middle of the 20th century, it retired from its Tavern days and became a private residence, making front-page news articles still.

The Black Horse Tavern still stands today, as a private residence and a mere shade of its former self (and minus a body chute, of course). Long gone are the days of a crowded and smoky bar, weary travelers, rowdy soldiers, creaking stagecoaches, and darkened back rooms where countless unnamed individuals met a grisly end. The tales around this historic place still loom large, swirling about the neighborhood of Sleepy Hollow Country much like the inky currents of the Croton River below it.