Beware the Headless Horseman! — Sleepy Hollow Country in NY State

My childhood was shaped by an eerie scene of cattails alongside a road that were beating, in the rising wind, a tattoo like ghostly hoofbeats upon a dark and lonely road.

I’ve loved Disney’s The Adventures of Ichabod and Mr. Toad (1949), an animated adaptation narrated by Bing Crosby, from the moment I first watched it on television, and viewing it every October is now an annual Halloween tradition. Despite the light-hearted ambience, the animated short very effectively captures the ghostliness of Ichabod Crane’s ride home through the haunted woods of Sleepy Hollow and his terrifying encounter with the Headless Horseman. (I now have it on DVD and can watch it whenever the mood strikes.)

“On mounting a rising ground, which brought the figure of his fellow-traveller in relief against the sky, gigantic in height, and muffled in a cloak, Ichabod was horror-struck on perceiving that he was headless!— but his horror was still more increased on observing that the head, which should have rested on his shoulders, was carried before him on the pommel of his saddle!” Washington Irving. The Legend of Sleepy Hollow

Well that would creep me out too!

The Legend of Sleepy Hollow is writer Washington Irving’s most famous and most beloved work. There’s something about Ichabod’s arrogance, brought down by a wild chase on a dark night, and the spectre of the rearing black horse and the apparition hurtling its head at Ichabod that has created a lasting impression on our collective imaginations.

Irving set his story in the Hudson River Valley of New York State, an area that had been embroiled in the American Revolutionary War. There was the Battle of White Plains in October of 1776, after which the countryside thereabouts was occupied by the British forces, while the Americans dug in north of Peekskill. In between the two, Westchester County was a lawless wilderness.

Among the various combatants and mercenaries, there was a group of Hessian Jägers, sharpshooters and horsemen from Germany who fought for the British. The character of the Headless Horseman in Irving’s short story was said to be one of those Hessian soldiers who was decapitated, and it may have been loosely based on the discovery of a real Jäger’s headless corpse in the locale of Sleepy Hollow and later buried by the Van Tassel family. The Van Tassel family existed in real life – you can see their graves in Sleepy Hollow cemetery – and Irving borrowed the name for the wealthy family in his story.

Additional inspiration for the Headless Horseman came from Irving’s travels through Europe, where headless horsemen often appeared in stories from Ireland to Germany to Scandinavia. In the tales, these horsemen usually afflicted people who were arrogant and scheming – just like Ichabod Crane in The Legend of Sleepy Hollow, who liked to get himself invited to his students’ homes for free meals and angled to marry the pretty Katrina Van Tassel for her father’s wealth. Irving wrote The Sketch Book of Geoffrey Crayon, Gent.,which included the famous ghost story, while he was staying in England, and clearly drew on all of these various influences.

Irving actually lived in Tarrytown twice in his life. His family was from Manhattan, part of the city’s merchant class. His mother named him after George Washington, and when Irving was six he even met his namesake when the president was living in New York city after his inauguration.

Irving was apparently an unenthusiastic student who loved adventure stories and regularly snuck out of class to go to the theatre. When he was fifteen there was an outbreak of yellow fever in Manhattan. Yellow fever  no longer exists in North America (it wasn’t original to our continent but had come over from Africa with the enslaved), but at the time it was considered one of the most dangerous infectious diseases, and so Irving’s family sent him upriver to stay with one of his friends in Tarrytown.

During that stay he took the opportunity to explore, making several trips up the Hudson River and through the Catskill Mountains that were to become the setting for Rip Van Winkle. He also became familiar with the nearby town of Sleepy Hollow and all its local ghost stories, and the entire area inspired him profoundly. “Of all the scenery of the Hudson”, he later wrote, “the Kaatskill Mountains had the most witching effect on my boyish imagination”.

He began writing when he was 19, under the pseudonym Jonathan Oldstyle, starting with a series of letters to the New York Morning Chronicle that were commentaries on the city’s social and theater scene. Still worried about his health, his brothers sent him on the tour of Europe for a while. When he returned, he began studying law in New York City, but still made an indifferent student and barely passed the bar exam. In the meantime, he’d begun socializing with a group of literate young men and created a literary magazine that was a moderate success, spreading his name and reputation.

And here’s an interesting little tidbit: it was Washington Irving who gave New York City the nickname “Gotham”, in the 17th issue of his magazine, from an Anglo-Saxon word meaning “Goat’s Town”.

Not long after, he began writing books, and the rest is, of course, history.

The Legend of Sleepy Hollow is the tale of a rather ridiculous man named Ichabod Crane, a schoolmaster from Connecticut who was already extremely superstitious by the time he arrived in the secluded glen of Sleepy Hollow, near the Dutch settlement of Tarry Town. Sleepy Hollow was renowned for its haunting atmosphere and numerous ghost stories. Residents claimed that the area had been bewitched during the early days of the settlement, and they often experienced various supernatural and mysterious occurrences. The most infamous spectre was the Headless Horseman, the “commander-in-chief of all the powers of the air,” who “rides forth to the scene of battle in nightly quest of his head”.

Of course, all of this fed into Crane’s imagination, and he loved to visit the Old Dutch wives and listen to their eerie stories. None of this would possibly have led anywhere were it not for Crane’s rivalry, with a rowdy local  hero named Abraham “Brom Bones” Van Brunt, for the hand of 18-year-old Katrina Van Tassel, the only child of wealthy farmer Baltus Van Tassel. Whatever Brom’s motives may have been, Ichabod saw dollar signs in a potential marriage to Katrina.

Brom, unable to force Ichabod into a physical fight for Katrina, ended up playing a series of pranks using Crane’s superstitions. Things came to a head one autumn night when everyone attended a harvest party at the Van Tassels’ homestead.

Throughout the evening Crane did his best to claim Katrina’s hand in marriage, but failed. Depressed, he left the party to ride home on his plodding mount, a plough horse named Gunpowder, through the woods between the Van Tassels and the farmhouse in Sleepy Hollow where he was staying. His progress was slow through the murky night, and after all the spooky stories he’d heard at the part, he grew increasingly apprehensive with each noise he heard. (If you’ve never experienced the almost absolute darkness of the countryside without electric lighting, I can tell you from personal experience that it is intensely unnerving.)

The journey took him past several famously haunted spots, including a lightning-stricken tree where the ghost of British spy Major André was said to hang out. As Ichabod neared the bridge adjacent to the Old Dutch Burying Ground, he was stunned to see a cloaked rider missing its head. Even more terrifying was the sight of the head perched on the rider’s saddle.

This could only be the spirit of the dreaded Headless Horsemen, and Ichabod’s only salvation would be to reach the bridge over the Pocantico River, which, according to legend, the spectre couldn’t cross.

“ “If I can but reach that bridge,” thought Ichabod, “I am safe.” Just then he heard the black steed panting and blowing close behind him; he even fancied that he felt his hot breath. Another convulsive kick in the ribs, and old Gunpowder sprang upon the bridge; he thundered over the resounding planks; he gained the opposite side; and now Ichabod cast a look behind to see if his pursuer should vanish, according to rule, in a flash of fire and brimstone. Just then he saw the goblin rising in his stirrups, and in the very act of hurling his head at him.” Washington Irving. The Legend of Sleepy Hollow

I won’t elaborate any further in case you haven’t read the story or watched any of the many film adaptations. Irving’s original story leaves it open to debate whether the spectre was real or another hideous prank by Brom Bones. The whole tale is so evocative that it has inspired numerous productions on film and television, including my favourite (the Disney version); the rather strange 1999 horror movie by Tim Burton that strayed pretty far from the original plot; episodes of Charmed and Ghost Whisperer; and a horror series I really enjoyed, Sleepy Hollow (2013 – 2017), which delved deeply into the Revolutionary War and Ichabod’s ‘actual’ role as an operative for George Washington, then getting resurrected in the modern day and battling the supernatural forces of the Four Horsemen of the Apocalypse.

Several years ago I was thrilled to discover that quite a few of the locales in Irving’s story actually exist, and can be visited. The entire Hudson River Valley is permeated with Washington Irving’s legacy and spirit, and makes a marvelous road trip in the autumn, when the entire area pulls out all the stops with Halloween-themed events.

When my hubby and I visited the first time (we loved it so much we repeated the trip just a few years later, and it’s within an easy drive from southern Ontario where we live), we based ourselves in Poughkeepsie, which is fairly central to all the interesting attractions. The valley itself is beautiful in October, with the Hudson River threading through all kinds of charming, well-preserved towns, magnificent turn-of-the-century estates and glowing fall colours.

Irving returned to Tarrytown (modern spelling) later in life and built his own home called Sunnyside (he was multi-talented). You can tour the house and grounds, and also participate in a variety of delightful Halloween programs for children and adults.

Within the vicinity, visit the actual town of Sleepy Hollow. You can stand on the Sleepy Hollow Bridge and wait to see if you hear ghostly hoofbeats, as well as take a tour of the Old Dutch Church and Burying Ground. Irving himself is buried in the cemetery, along with the real Van Tassel family and, more contemporary to us, quite a number of famous people like the infamous hotel queen Leona Helmsley. Apparently the real headless Hessian soldier is also buried somewhere there, in an unmarked grave. The cemetery had just begun offering tours the first year we went, and the tours have grown enormously in popularity ever since.

There are numerous lavish and/or historic estates, from the Gilded Age ‘cottage’ of the Vanderbilts to exotic Olana (the home of famous Hudson River School artist Frederick Church) to Clermont State Historic Site, dating back to the mid-1700s. The Livingstone family that built it was involved in the Revolution, and when we were there the estate held a recreation of a 1920’s Halloween party for the children, where the ‘spirits’ of deceased family members made a guest appearance both inside and out on the evening ghost tour.

One of the most fascinating places to visit, even for we Canadians, is the lifelong home and estate of Franklin Delano Roosevelt in the town of Hyde Park in Dutchess County. There’s an enormous amount of history there, and the house had many famous visitors, including Queen Elizabeth II and Winston Churchill. Out back you’ll find the Peace Garden, which holds two pieces of the Berlin Wall carved into silhouettes. The grounds are extensive and great to explore, and as Canadians we were amused to see a very large flock of Canadian geese taking over the front lawn.

The valley is peppered historic small towns (including our personal favourite, Rhinebeck) filled with beautiful old homes, cool shops (the town of Hudson is renowned for its antique stores) and interesting places to eat (see the Beekman Arms in Rhinebeck, a pre-Revolution inn with a delightful tavern and good food).

There are wonderful farm markets to explore as you drive around (we had the best chocolate milk ever from the Wayside Stand of the Montgomery Place Orchards, operated by the gorgeous Montgomery Place Estate, which houses Bard College). In the autumn, look for any place with piles of pumpkins for sale!

All of the estates have gorgeous rolling properties along the Hudson where you can spend hours strolling, so do wear hiking-worthy clothes and shoes, and bring your camera!

The haunted offerings are plentiful. Two of our favourites (more have sprung up since we were there) are: the Great Jack O’Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson, where more than 7,000 illuminated carved pumpkins light up the night in various configurations on a night-time stroll through the property (there’s also a fabulous gift shop at the end!); and The Headless Horseman Hayrides and Haunted Attractions in Ulster Park on the west side of the river. The Headless Horseman is the coolest haunted attraction hubby and I have ever been to – 65 acres of: haunted corn maze, a superb 20-minute hay wagon ride through the creepy woodland trails and lots of scares, several haunted houses, several incredible shops filled with some very stylish Halloween merchandise, refreshment stands and more. You’ll need to book tickets and an entry time before you arrive, but once you’re inside you can stay as long as you want. The theme changes every year, so you won’t see the same thing twice. This place is very highly-rated and I can’t say enough about it. Cameras aren’t allowed inside, so I can’t show you any personal photos, but you can get a very good idea on the website.

If you’re a fan of the original 1960s television series Dark Shadows, Lyndhurst estate will be a mecca for you: it was used for the exterior shots in the two movies, House of Dark Shadows (1970) and Night of Dark Shadows (1971). The lavish mansion at different times housed some of the cream of early-20^th-century New York society, including mayor William Paulding, merchant George Merritt and railroad tycoon Jay Gould. You can take tours of the house and explore the grounds. This year in October Lyndhurst is hosting a Dark Shadows Meet & Greet with two of the stars of the tv series, Kathryn Leigh Scott, who played “Maggie Evans” and “Josette DuPres” and Marie Wallace, who played “Eve”, “Megan Todd” and “Jenny Collins”.

There’s so much going on in ‘Sleepy Hollow country’ in NY State that even with two visits my hubby and I haven’t come close to seeing everything – which just means we’ll have to go back for a third 😉 In fact, there’s too much to tell you about in this post, but there are numerous sites where you can do some research to make your own shortlist for how ever long you’re able to be in the area (see below). I’ve provided links to many of our favourites, but I suggest you sit down one afternoon with a cup of tea and maybe a pumpkin scone and do some armchair exploring online.

• Visit Sleepy Hollow
• I Love NY, Hudson River Valley
• Hudson Valley Tourism
• Hudson River Valley Heritage Sites
• Lonely Planet – Hudson Valley
• Trip Advisor

Whenever you decide to go, have a hauntingly good time!