The Headless Horseman and the Battle of White Plains thumbnail

The Headless Horseman and the Battle of White Plains

By Catherine Salgado

Estimated Reading Time: 4 minutes

On Oct. 28, 1776, at the Battle of White Plains in New York, a Hessian soldier lost his head — literally. But for two and a half centuries he has haunted Americans’ imaginations as the Headless Horseman of Sleepy Hollow.

If you go to the village of Tarrytown, New York, still today, as I did this year, you can see the Old Dutch Church and cemetery which the Headless Horseman once haunted. You can see the tombstones from which Washington Irving drew the names in his spooky legend, including the real Catriena Van Tassel. You can walk the woods that British spy John Andre supposedly haunted after the Americans hanged him, and you can sit on the porch of Washington Irving’s home and watch the clouds form ever-changing patterns over the Hudson river which he loved. Tarrytown is no longer the quaint Dutch colonial town which so captured Irving’s heart, but it retains its old-fashioned charm and a lurking touch of the ghostly influences that inspired the quintessential American ghost story: “The Legend of Sleepy Hollow.”

As I noted above, we just marked the anniversary of the American Revolution’s Battle of White Plains, in which Washington and his men suffered a defeat but did succeed in escaping the British. The battle occurred only a few miles from Tarrytown.

The New-York Historical Society notes that Maj. Gen. William Heath wrote the following in his memoir: “A shot from the American cannon at this place [White Plains] took off the head of a Hessian artillery man.” Years later, Irving thus described the Headless Horseman:

It is said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannon-ball, in some nameless battle during the [R]evolutionary war; and who is ever and anon seen by the country folk, hurrying along in the gloom of night, as if on the wings of the wind…he sometimes passes along the Hollow, like a midnight blast.

Irving’s legend detailed the adventures of Ichabod Crane the Yankee schoolmaster, an “odd mixture of small shrewdness and simple credulity.” Crane was a superstitious man who came among equally imaginative Dutch settlers. The schoolmaster fed his scared brain a diet of local folktales and Puritan Cotton Mather’s History of New England Witchcraft. On the “long winter evenings with the old Dutch wives… [he] listen[ed] to their marvelous tales of ghosts and goblins, and haunted fields, and haunted brooks, and haunted bridges, and haunted houses, and particularly of the headless horseman, or galloping Hessian of the Hollow, as they sometimes called him.”

But, as Walt Disney and Bing Crosby would put it in their retelling, Crane’s existence was disrupted when he crossed paths with a woman — the lovely and wealthy Katrina Van Tassel. But, Irving told us, Katrina already had a suitor, Brom Van Brunt or “Brom Bones,” “the hero of the country round, which rang with his feats of strength and hardihood.” And Brom Bones, who was about as opposite to a ghost as it is possible to be, was soon aching for an opportunity to revenge himself on the love-lorn and money-worshipping schoolmaster.

Balt Van Tassel, Katrina’s father, threw a party which displayed all the best food and dancing in the vicinity. Brom Bones, jealous of Ichabod’s rousing success as a dancer, joined in the telling of ghost stories by asserting that he himself had met the Headless Horseman and even challenged him to a race — which Brom asserted he won. As Brom guessed, he filled Crane with ghostly foreboding, only augmented by Crane’s dismissal by Katrina that night.

“It was the very witching time of night” when Ichabod Crane set out home. The schoolmaster had just arrived at the haunted stream where John Andre was captured, when he suddenly saw “a horseman of large dimensions, and mounted on a black horse of powerful frame” — and headless!

The Headless Horseman was “gigantic in height, and muffled in a cloak,” and the terrified Crane desperately tried to force his old horse to out-race the apparition at the Old Dutch Church, seeking to reach the old bridge, at which the headless Hessian is supposed to vanish. But after successfully crossing the bridge, Ichabod found the bone-chilling Horseman was hurling his severed head after him! “Ichabod endeavored to dodge the horrible missile, but too late. It encountered his cranium with a tremendous crash — he was tumbled headlong into the dust, and [his horse], the black steed, and the goblin rider, passed by like a whirlwind.”

When morning dawned, locals found a shattered pumpkin and Ichabod’s hat lying by the bridge, but no schoolmaster. One farmer later asserted Ichabod left in a fever of shame and horror and became a justice of the Ten Pound Court. To make it more suspicious, Brom Bones, who did indeed marry Katrina, always laughed uproariously and delightedly and looked very “knowing” when the story was told. But the “old country wives” knew perfectly well, Irving said, that “Ichabod was spirited away by supernatural means.”

Over a century later, Walt Disney agreed with the old country wives, and he re-popularized Ichabod Crane and the Headless Horseman for new generations in his movie “The Adventures of Ichabod and Mr. Toad.” To narrate and sing the iconic legend, Disney chose Bing Crosby, the celebrity nicknamed the “Voice of America.”

And truly we can say that Washington Irving was also the Voice of America, melding history, fantasy, and fancy together into an unforgettable and unsurpassed Halloween tale.

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