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.

II.

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.

III.

Genuine Tarrytown ghost stories like that of the Galloping Hessian, the sighing spirit of poor Major Andre (captured by Skinners at Andre’s Brook and hanged a month later for espionage), and even the weeping Woman in White at Raven Rock (said to have died during a blizzard after being abandoned by her Loyalist lover) speak to the area’s deep code of local chivalry.

Sleepy Hollow demands that its immigrant residents either become converts to the Sleepy Hollow way of life – to assimilate psychologically to a lifestyle of moderation, imagination, unambitious peace, and collaborative community – or to be expelled. There is a strong sense that the community protects itself from outsiders, invaders, and opportunists – and this, after all, is the “legend” of Sleepy Hollow: come in if you’d like, assimilate if you can, but be prepared for hard riding if you try to mess with us. And Ichabod does just that.

As many commentators have noted, Ichabod – a consummate individualist and loner – never seems to understand the advantages of community and fellowship. In one memorable episode, he is stunned that his schoolhouse’s security system was hacked, but fails to realize that while a single burglar would be stuck by the window stakes, a group of two or more – helping each other – could easily skirt around his precautions.

Ichabod thinks like a loner and never appreciates Sleepy Hollow’s small-town ethos. Many readers skim over the part of the story where Ichabod fantasizes about liquidating the Van Tassel farm and taking Katrina – and a wagon load of Crane-Van Tassel children – to “Kentucky, Tennessee, or the Lord knows where.”

Irving suggests that it is part of his Yankee spirit (New Englanders, as he says, provide the country “with pioneers for the mind as well as for the forest, and sends forth yearly its legions of frontier woodmen and country schoolmasters”). In “Knickerbocker’s History,” Irving unfavorably contrasts the ambitious, pumpkin-eating New Englanders – crafty, hypocritical schemers itching for profit in contrast with their Puritan values – with the easy-going, simple-living, dull-witted Dutchmen.

Writing as Knickerbocker he represents this archetype in the form of noble Baltus – a paradigm of open-minded liberality. The virtual personification of Sleepy Hollow, Baltus doesn’t let the worries of the outside world taint his domestic contentment. Unlike Ichabod (and by proxy, the modernizing cities teeming with ambitious social climbers and unrooted opportunists), Baltus doesn’t see the grass as greener on the other side: he loves his farm, his family, and his community, and his is a life of peace and contentment.

Not so Ichabod: he doesn’t want to replace Baltus – to become the next lord of Sleepy Hollow – he wants to liquidate his legacy, sell off the property to outsiders, pocket the cash, and leave Sleepy Hollow in the hands of strangers. If Ichabod marries Katrina, it will be the end of the community as they know it. No longer will it be a tight-knit, cozy village of neighbors; instead, it will be given over to investors, speculators, and real estate moguls.

This is why Brom’s fight against Ichabod isn’t just for Katrina: it is for Sleepy Hollow’s soul. Note that while Brom is usually depicted as a villain, that he is highly esteemed by the Sleepy Hollow residents, and viewed as something between a judge, trickster, hero, and heartthrob. While Baltus is the king of the Hollow, Brom is its warrior-protector.

Ichabod, on the other hand, is a villain worthy of a Shakespearean comedy: much like Malvolio in “Twelfth Night,” Shylock in “The Merchant of Venice,” or Nick Bottom in “A Midsummer Night’s Dream,” Ichabod is ludicrous for his lusty ambition, high self-estimation, physical awkwardness, and his confidence in his ability to dance, woo, and make love. In the end – as in most of Shakespeare’s comedies – the leering villain is cathartically humiliated in a harmlessly hilarious way.

Chased off and humbled, he returns to his proper station in life: in Ichabod’s case he becomes what Irving most loathed – a petty politician and a small-claims lawyer. No fate of any character is more pathetic and lamentable in the Irvingian universe than Ichabod’s – while Balt cozily smokes his pipe on his porch and Brom flies down the rolling roads of Sleepy Hollow, Ichabod is buried in paperwork, clawing for every shilling he can grasp, and putting his sycophantic personality to good work.

While Ichabod – like the mercenary Hessian and the plotting Andre – threatens to bring chaos and change to the time-frozen community, two local agents are responsible for its fate, and serve as exemplars of their respective genders: Brom and Katrina. Brom represents Sleepy Hollow masculinity: easy-going and sincere, yet chivalric and rustic, while Katrina represents Sleepy Hollow feminity: self-aware and empowered, yet watchful and coy.

Katrina is on the precipice of Sleepy Hollow’s community and culture: just as comfortable in traditional garb as she is in modern fashions, she is equally likely to stay in Sleepy Hollow and continue her family traditions, or to be whisked away to some new, progressive place.

Katrina holds the future of Sleepy Hollow in the balance: will she stay and nurture it with her beauty, intelligence, and fortune, or will she leave it to age and die in the company of an outsider man? Ichabod’s seductive sway over females is a recurring pressure point on the community throughout the story: impressed by his “learning,” they quickly tire of their male counterparts – the strong, rough-housing Dutch lads – creating a crisis of masculinity in Sleepy Hollow.

With Katrina as the jury, and Sleepy Hollow’s future on trial, Ichabod serves as the prosecutor, challenging Sleepy Hollow’s gender norms and providing and alternative masculinity: sly, intelligent, scheming, and opportunistic. In truth, Ichabod’s plan to move to Kentucky (which will probably involve developing a plantation and the use of slave labor) has more opportunities for wealth than continuing her father’s legacy in overcrowded Westchester.

The case is made, and the stakes are high. Brom, on the other hand, acts as Sleepy Hollow’s public defender, making its case to Katrina. Note that Irving capitalizes BROM BONES just as he had capitalized SLEEPY HOLLOW. Brom and Sleepy Hollow are one and the same: Brom advances the community’s agenda, serves as its mascot and spokesman, and protects its interests from the schemes of interlopers like Ichabod.

Ichabod is not lured by human companionship and community – not even the company of beautiful women – but by the self-serving attractions of food, wealth, and appetite. If he was lecherous and bawdy, even that – crass as it would be – would have a humanizing effect on his largely self-serving, lone-wolf personality that is more motivated by gratifying its need to consume than by a desire for community and human connections.

This is, in part, why Ichabod is so terrified of ghosts, and why Brom slyly employs local folklore as the coup de grace to drive Ichabod out. “Ghosts” – to Irving – represent culture, community, and fellowship, and ghost story telling operates as a social ritual meant to strengthen and weld communities through their shared narratives.

IV.

A town which perpetuates its unique legends, then, must be a socially and spiritually healthy place where bonds and connections continue to be fostered. Ichabod proves to be cocky and vain when in company, but existentially woeful whenever alone: he loves listening to wild tales by the fire, but dreads the necessitated walk home by himself. Ichabod – by nature a self-seeking, individualistic lone wolf, with no concern for community or fellowship – is forced to confront his vulnerability and uprootedness whenever he is alone: he is forced to realize that he is himself a ghost. His confrontation with the Headless Horseman is a confrontation with reality – a glance into a mirror, a look exchanged with his Doppelgänger.

Like Andre, the spy, and the mercenary Hessian, Ichabod is yet one more casualty of Sleepy Hollow: a community that kicks back against invaders, users, and opportunists. Andre had sought to subject the community for his king, the Hessian for pay, and Ichabod for his ambition, and all three are lost into the vortex of Sleepy Hollow’s terrible revenge.

This is the “legend” of Sleepy Hollow: the moral that those who take advantage of our hospitality – those outsiders who seek to use and disenfranchise us for their own personal gain without any investment into our community or fellowship – will be promptly evicted, or otherwise, destroyed.

But in the end, we are never meant to believe that – whether the actual Horseman is real or not – the figure encountered by Ichabod was supernatural. The pumpkin alone – a bit of visual rhetoric pointing him back to New England’s pumpkin patches – along with Brom’s knowing chuckle are enough to clue us in.

Brom’s tale of his encounter with the Hessian is also telling: in Brom’s story he finds kinship in the Hessian as a fellow lover of horse racing. This not only telegraphs Brom’s eventually role as the Headless Horseman, but further cements his reputation as the personification of Sleepy Hollow and its people: the Horseman – horror of skeptics and outsiders – is no threat to him; merely a chummy comrade.

Using the community’s ghost stories – narratives meant to illustrate reality through the lens of imagination – he frightens off Ichabod with a headless figure. The Hessian’s lack of a head and face are his most frightening features – separated from his visage, he is symbolically divorced from his identity: an anxiety that haunts Ichabod’s insecure ego.

A symbol of anonymity and existential annihilation, the Horseman is faceless, featureless, nameless, and friendless, symbolizing the manner by which Sleepy Hollow avenges itself – by taking ownership of its enemies’ identities, repurposing them for their “legend” and twisting them however they like to fashion a new identity – or lack thereof.

And this stabs at the heart of Ichabod’s insecurities: Irving interestingly alludes to Crane’s psychological state – the brooding insecurities that seem to be constantly simmering below his personality. Depression, loneliness, anxiety, and self-doubt blend with arrogance, egotism, vanity, and pride. The former attitudes thrive in the darkness – the lonely hours, where his existential ennui is let loose – while the later thrive in the light – at work, at parties, at social visits. At his core Ichabod is bifurcated personality torn between self-loathing and rampant egotism. His race with Brom only acerbates those sensitivies, and by confronting Ichabod in the shape of his future self – a faceless, friendless phantom – he successfully dislodges the invader and rescues Sleepy Hollow for posterity.

V.

Yet Brom is not alone. As quiet and helpless as she may have seemed at first (though most readers are immediately alerted by her self-awareness), Katrina has an even more powerful role in Sleepy Hollow’s defense. She had, after all, rejected his proposal before Brom even delivered the final, phantasmic blow. Throughout the story Katrina has seemed like a helpless commodity being bartered for between two merchants, but in reality she has been in control of the entire situation: channeling Brom’s wild nature and love for her by engineering the ludicrous obstacle of Ichabod.

Without Ichabod, Brom – like the perpetual bachelor Washington Irving – would have been content to spend his days riding, roughhousing, and hanging out with the Sleepy Hollow Boys. Katrina – savvy to his chivalrous nature – decides to goad him into commitment by manipulating Ichabod’s vanity. Having secured Brom’s determination to win her back during the party (Brom’s visible jealousy and heartbrokenness during the dance would be all too telling), she sees no reason to string Ichabod along any further, and releases him.

A proto-feminist heroine, Katrina subverts the expectations of her patriarchal society, turning the tables on the men, and gaining control of her courtship through intellect and intuition. And her ultimate choice is made in her best interest: remember that Ichabod’s fantasy involves Katrina serving him food with as much emotional connection between them as a waitress/costumer or servant/master.

On the other hand – at almost the same time that Ichabod is lusting over the idea of Katrina’s “dimpled hand” buttering his desserts, Brom Bones is agonizing over her inattention, sitting in a corner “sorely smitten with love and jealousy.”

Note that Irving lists love before jealousy: unlike Ichabod, Brom truly loves Katrina, and his jealousy is not rooted in his vanity (like Ichabod’s), but in his heart. Far from the “Beauty and the Beast’s” Gaston-like macho villain that many versions turn him into, Irving’s Brom is a gallant figure of rustic chivalry ruled by high values and integrity unlike the people-pleasing pedagogue.

Apparently Katrina is not merely a coquette after all, but rather a sly engineer of her own destiny. By wedding Brom (the masculine ideal of Sleepy Hollow manhood: just, open-handed, open-hearted, unblushing, integral) she (the feminine ideal of Sleepy Hollow womanhood: intelligent, spirited, independent, and savvy) fuses the gap created by Ichabod’s appearance, and order is restored to Sleepy Hollow.

VI.

Today we still fondly remember the story for its blend of humor, fantasy, romance, suspense, and mystery, and it seems to speak deeply to people who come from small towns with quirky personalities – averse to modernization. Irving was always an egalitarian for taking pot shots at heel-dragging conservatives as well as near-sighted radicals, so he must have seen Sleepy Hollow as more than a backwards, backwoods, backwater town fighting in vain against progress. Indeed, Sleepy Hollow seems agreeable to change that doesn’t challenge its very identity. Ichabod is initially accepted along with his marvelous tales of quack science and New England superstitions, and the young people don city fashions without censorship from their old-fashioned-but-easy-going parents.

Irving paints the portrait of a community that accepts outsiders willingly – with the understanding that contact with Sleepy Hollow will invariably change its visitors regardless of how briefly they tarry there. Sleepy Hollow isn’t impervious to all change, but is specifically allergic to urban paternalism and “improvement.”

As Knickerbocker says, “I mention this peaceful spot with all possible laud, for it is in such little retired Dutch valleys, found here and there embosomed in the great State of New York, that population, manners, and customs remain fixed, while the great torrent of migration and improvement, which is making such incessant changes in other parts of this restless country, sweeps by them unobserved.”

Ever the moderate, Irving’s Knickerbocker breathes this word with suspicion and woe. “Improvement” means the elimination of folk culture. Perpetually rootless, the cosmopolitan Irving deeply appreciated Sleepy Hollow’s resistance to modern influences: to him it was predictable, stable, and authentic – as untainted by artifice or fashion as its rocks, trees, and brooks. At its root, that is what this story is about: authenticity being bombarded by hypocrisy, sincerity being besieged by flattery, truth being assaulted by falseness, open hearts being undermined by hidden motives.

But even liberal-hearted, open-handed Sleepy Hollow has a secret that it has cultivated over the years – a hidden defense against intruders and improvers – a concealed thistle in its otherwise bucolic flowerbed. It is willing to fight back – believe it or not – between siestas and daydreams. It is willing to preserve its unique culture and to defend its way of life.

Perhaps this was a political message about the American character during a time of concern about foreign interference. Perhaps it was merely a humorous way of caricaturing Americans’ confusing blend of laissez-faire and spirited self-defense. But whatever Irving meant by it, it has remained part of Americans’ cultural identity for two centuries, and still shapes their identity today.

You can find our collection of Washington Irving's best ghost stories, annotated and illustrated, HERE!