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Critical Editions of Classic Ghost Stories & Weird Fiction

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Washington Irving's The Legend of Sleepy Hollow: Historical Backgrounds & a Deep Literary Analysis

On a hot afternoon in the summer of 2008, I found myself standing on a concrete bridge thirty miles north of New York City, watching the black water of a lazy brook drift into the shadow of yawning trees. Above me the Old Dutch Church rested on a green knoll, where, hard by, Washington Irving’s small, white grave overlooked the old Albany Post Road, where his busybody pedagogue (a prancing caricature fit for one of Shakespeare’s comedies) once raced the Headless Horseman. I was in Sleepy Hollow, and at 21 I still felt the magic and awe that had first drawn me to Washington Irving’s somnambulant universe.

It was more than a story, to me, it was a state of mind, and different as it was from Irving’s 18th century settlement, it still slumbered in the afternoon heat like a snoozing, old Dutchman dreaming of ghost ships gliding up the Hudson. Outshined only by “Rip Van Winkle,” “The Legend of Sleepy Hollow” remains Irving’s pop-culture masterpiece. While other stories have more literary merit, few have grappled the public’s imagination as fiercely as this uniquely American fable of greed, fear, and community.

Two of the tale’s elements have ensured its immortality and justified its popularity for over two centuries. The first is the love triangle between a brainy pretender, a brawny protector, and the prettiest girl in town. When I teach this story to my classes, it doesn’t take much to draw them to its archetypal nature: it is the story of the geek and the jock vying for the cheerleader; it’s “Cyrano de Bergerac,” “The Courtship of Miles Standish,” “The Great Gatsby,” “Gone with the Wind,” “Casablanca,” “A Tale of Two Cities,” “Twelfth Night.”

The mythic nature of this struggle for possession over the female ideal – patriarchal baggage included – resonates with us deeply. Which is more valuable: intelligence or strength? Ah, but what if the intelligence is sly and the strength is sincere? We find ourselves balancing Ichabod and Brom in the scales of our own judgment – like a good friend, we want to help Katrina make the best choice for her happiness and future. Irving’s characterization may be slight (only a few words of dialogue are delved out, and they are largely shrouded in mystery) but the three main characters are utterly universal. We have all known a Brom, an Ichabod, and a Katrina.

The second element that has worked in the story’s favor is the Hallowe’en holiday, and the coincidental history of a single vegetable. Everyone pictures the Headless Horseman flourishing a flaming jack-o-lantern over his head – complete with ghoulish grin – but Irving’s choice of false head took place nearly twenty years before pumpkins began usurping turnips as the traditional jack-o-lantern vegetable (Irish immigrants from the Potato Famine found that American pumpkins made far better lamps than Irish turnips).

For Irving, the pumpkin was a symbol of Crane’s native New England (“pumpkin eater” was a pejorative term for a Yankee), and Brom’s use of it was like hurling cheese at a Wisconsinite, pretzels at a German, or herring at a Swede. The unintended coincidence of the pumpkin, the ghost story, and the autumnal setting (Irving never says that it is set on Hallowe’en, merely in the midst of “jolly autumn”) has cozily knit “The Legend of Sleepy Hollow” into the cultural fabric of Hallowe’en. Nearly every state in America has a Headless Horseman hayride, not to mention at least a dozen cities named Sleepy Hollow renowned for their Hallowe’en celebrations. Another part of the thrill that has lured so many readers over the centuries is the undeniable historicity of so much of the plot.

Not only is Sleepy Hollow a real place (viz. the Pocantico River Valley, downriver of the Old Dutch Church, and today almost entirely unspoiled as part of the Rockefeller State Park Preserve), but most of the characters have historical models. Katrina is based on the spirited Eleanor Van Tassel, Brom on the blacksmith and Revolutionary War hero Brom Martling, and Ichabod on Kinderhook schoolmaster Jesse Merwin.

The places can all largely be visited today in Sleepy Hollow and Tarrytown, New York: the Old Dutch Church and Burial Ground (where a pumpkin is annually left on Martling’s grave and Eleanor’s can still be found), the black, rolling brook (the Pocantico), and the two models for the Van Tassel Manor (Irving’s Sunnyside and the Van Cortlandt Manor in nearby Croton-on-Hudson).

You can also find the fearsome glen of Wiley’s Swamp (modern Patriots Park), Ichabod’s trail home (precisely three miles along New York Route 9: from Sunnyside to the Old Dutch Church), the haunted crag of Raven Rock (on Buttermilk Hill in the State Park), and of course Sleepy Hollow itself – the silent and magisterial Pocantico River Valley winding through the Preserve. Irving also laced his story with authentic superstitions: the wailing woman at Raven Rock, the ghost of Major Andre (and his massive tulip tree), and the Headless Horseman himself are all authentic Westchester County legends. What draws most readers to the story, in fact, is the very genuine sense of place and community that it has – the sleepy little town with buried secrets, delicious love triangles, and a powerful past.


These were elements that Irving did not need to manufacture: he exported them from his experiences shooting squirrels in the Sleepy Hollow woods and spending time with the drowsy residents. The fictional version of Sleepy Hollow is disarmingly sublime, but also deceptively defensive: it has a history of welcoming new comers with open arms and watchful eyes – and of violently evicting them if friend dares to become foe. Such was the fate of the Headless Horseman (a mercenary paid to subjugate the county Whigs under British rule) and of Major Andre (a spy who paid Benedict Arnold to hand over nearby West Point).

And Ichabod Crane, too: a scheming carpetbagger who hopes to marry the local belle for her father’s fortune, to liquidate it, and to take the cash with him to the Western Frontier, leaving Sleepy Hollow’s economy deflated and its history vulnerable to the intrusions of other opportunistic outsiders.

The actual “legend” of Sleepy Hollow isn’t the ghost story of the Headless Horseman, or even that of Ichabod Crane. The “legend” is the town’s self-constructed identity, and philosophical method of dealing with invaders – we let them come here if they want, assimilate if they want, but if they try to mess with our community, they’ll join Andre, the Hessian, and the others. The “legend” isn’t a fable or a rumor or a wives’ tale. The “legend” is a warning…

Like “The Sketch Book’s” other Gothic masterpieces, “The Spectre Bridegroom” (“Lenore”) and “Rip Van Winkle” (“Peter Klaus”), “The Legend of Sleepy Hollow” borrows from European folklore, infusing the grim self-importance of the source material with burlesque self-deprecation – giving it a uniquely American atmosphere without compromising the sense of Old World wonder.

In the case of “Sleepy Hollow,” the sources are multiform: Karl Musäus’ satirical fairy tale, “The Legend of Rübezahl” (which tells of a Puck-like imp disguising himself as a headless rider and brandishing a turnip like a head), Robert Burns’ delightfully burlesque Gothic misadventure, “Tam O’Shanter” (wherein Tam and his haggard mare are chased by a coven of witches who disappear once he crosses the church bridge), and G. A. Bürger’s “The Wild Huntsman” (describing the transformation of a cruel nobleman into a ghost doomed to ride on the wings of the wind).

Although somewhat anecdotal, another source for the story may come from the original Ichabod himself: Jesse Merwin of Kinderhook. The story goes that Merwin was chased through the woods by a shrouded figure – a prank meant to force him to commit to his long-suffering fiancée, Jane Van Dyk. Bothered by Merwin’s dragging of his heels to the altar, mutual friends met and designed a charivari – a rustic custom meant to frighten ambling lovers into either marrying or call it quits.

One night, after leaving Jane Van Dyck’s house, Merwin found himself being followed by a goblin-like horseman muffled in a cloak. The stalking developed into a race, with the shapeless specter suddenly disappearing in a cackle of familiar laughter. Taking the hint, Merwin proposed and married Jane rather than suffer a lifetime of similar assaults.

There is also, of course, the historical superstition of the Headless Horseman of Sleepy Hollow. Irving first heard of the apparition as a child, from an African-American retiree at Carl’s Mill – considered the local haunted house – downriver from the Church. Such a superstition would be understandable. During the Revolutionary War, Westchester County was a practical wasteland of vigilantism, wild west justice, pillaging, raids, heroics, villainy, and anarchy. Sandwiched between the Patriot lines at Peekskill and the British lines at Kingsbridge, it became referred to as “the Neutral Ground,” but was really a wild no-man’s land of lawlessness.

Dozens of brutal skirmishes were recorded between Patriot and Loyalist militias, at least one full-scale battle at White Plains, and countless raids on civilians by the so-called Skinners (Patriot-allied bandits) and the Cowboys (British-allied raiders) – either of whom could switch loyalties for money. Tarrytown was raided by the British at least twice and shelled once, and a cannon was fortified just south of the Old Dutch Church to protect Philipsburg Manor from attacks by Hessian troopers (the notorious Jaeger chasseurs) and British light infantry.

Many harrowing adventures took place in the area, including the famous 1777 raid on the Van Tassel farm (where the two Van Tassel brothers were captured by a mixed force of Hessians and Loyalists, their house burned, and their cattle stolen; meanwhile young Elizabeth Van Tassel’s daughter Leah was saved from the fire by a Hessian soldier, who also saved the two from freezing by bringing them a quilt). Hessian troopers – also called chasseurs or dragoons – in their crimson-trimmed green jackets, were among the most feared adversaries of the Patriots.

Equipped to fight on foot or horseback, armed with light cavalry sabers, pistols, and rifles, they were almost all former foresters (or rangers) paid to range their king’s private woodlands, and were as skilled sharpshooters, riders, and trackers as the infamous Yankee riflemen. A local legend claims that one morning the headless corpse of a Hessian dragoon was found on the Albany Post Road. Remembering the kindness of the German who saved her and her baby, Elizabeth Van Tassel arranged for the stranger to be buried in the Dutch cemetery. His unmarked grave can still be pointed out by the church sexton.