Washington Irving’s Iconic New York Stories

Washington Irving’s Iconic New York Stories:  Rip Van Winkle and The Legend of Sleepy Hollow

By Susan Ingalls Lewis

John_Quidor: Headless Horseman Pursuing Ichabod Crane (Smithsonian)

John Quidor: Headless Horseman Pursuing Ichabod Crane (Smithsonian)

Despite the fact that he spent many of his productive years abroad, Washington Irving (1783-1859) was a quintessential New Yorker.  The man who coined the nicknames Gotham for New York City, and Knickerbocker for New Yorker also enshrined the Hudson River village of  Sleepy Hollow (formerly North Tarrytown) and the Catskill Mountains in the collective American memory.  His fictional characters Rip Van Winkle and Ichabod Crane are recognizable to most of us today through various adaptations of their stories (some having very little relationship to the originals, as with the current Fox series Sleepy Hollow, a surprise hit just renewed for a second season).  What witches are to Massachusetts, the Headless Horseman is to New York State; The Legend of Sleepy Hollow is New York’s ultimate Halloween story.  In fact, after the village of North Tarrytown lost its General Motors assembly plant in 1996, it actually changed its name to Sleepy Hollow to increase tourism, and the new TV series has furthered that goal.

Sunnyside_Tarrytown_Currier_and_Ives_crop_closeupIrving’s most famous stories are not just part of New York State history because he was from New York – born in New York City, died in his cottage Sunnyside (now a National Historic Landmark) in Tarrytown—but because they also reflect the history of the period in which he lived and wrote.  Rip Van Winkle highlights the difference between New York as a pre-Revolutionary provincial backwater and a growing state; after his twenty-year sleep, Rip awakes to find that the “very character of the people seemed changed. There was a busy, bustling, disputatious tone about it, instead of the accustomed phlegm and drowsy tranquility . . .”   Though Irving is exaggerating colonial New York’s lethargy for literary effect, the period following the Revolution—the Early Republican period—was precisely the time when New York began to surpass other states in population, commerce, and industrial development.  The changes Rip notices are the very changes that had happened in Irving’s own lifetime (he was in his mid-thirties when these stories were written).  Similarly, Irving’s nostalgia for the “old” New York is evident in this paragraph from The Legend of Sleepy Hollow:

. . . 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.


Although Irving had never explored the Catskills at the time he was wrote these stories (he had only sailed past them on a trip up the Hudson), he had visited Tarrytown several times in his youth.  The countryside, landmarks, and even family names like Van Tassel can be recognized and traced.  The Legend of Sleepy Hollow is the longest of the 25 “sketches” that make up The Sketchbook of Geoffrey Crayon, Gent., Irving’s first international best-seller.

Like Rip Van Winkle, The Legend of Sleepy Hollow reveals Irving’s sensitivity to the landscape of the Hudson Valley and an appreciation of its bounty.  Locating the “sequestered glen” of Sleepy Hollow on the east bank of the Hudson two miles from Tarrytown, Irving’s fictional narrator, Dietrich Knickerbocker, paints a lyrical image of:

. . . a little valley, or rather lap of land, among high hills, which is one of the quietest places in the whole world. A small brook glides through it, with just murmur enough to lull one to repose; and the occasional whistle of a quail, or tapping of a woodpecker, is almost the only sound that ever breaks in upon the uniform tranquillity. . . . if ever I should wish for a retreat, whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.

Joe Jefferson as Rip Van Winkle

Joe Jefferson as Rip Van Winkle

Yet this “drowsy, dreamy” corner also “abounds with local tales, haunted spots, and twilight superstitions; stars shoot and meteors glare oftener across the valley than in any other part of the country . . .”  So Irving sets the scene of what one might expect to become a rather atmospheric, if tame, ghost story.  Instead the tale soon turns into a satire.

How does Irving’s satirical ghost story, written in Europe and based on a German folktale, reflect New York State history in the Early National period?  Most obviously, the ghost is a Hessian mercenary, doomed to search nightly for his missing head—blown off by a cannon ball during the Revolutionary war.   But I think we can dig deeper by comparing the two male leads and rivals for the hand of Katrina Van Tassel:  the “Yankee” Ichabod Crane and the “Dutch” Brom Bones.  According to Irving, Crane “was a native of Connecticut; a State which supplies the Union with pioneers for the mind as well as for the forest, and sends forth yearly its legions of frontier woodsmen and country schoolmasters.”  Like other New England states, Connecticut had too many young men and too little free land for them all to inherit enough land to become farmers.

Though Ichabod Crane may be the protagonist in Sleepy Hollow, in the original story he is in no way the hero of the tale.  The New England school master was:

. . . tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together. His head was small, and flat at top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a weather-cock, perched upon his spindle neck . . . To see him striding along the profile of a hill on a windy day. . . one might have mistaken him for . . . some scarecrow eloped from a cornfield.

This unattractive picture of Crane is supplemented by snide observations on his character. The reader sees the teacher as a figure of fun, who ingratiates himself with the local families that pay his salary, especially those with “who happened to have pretty sisters, or good housewives for mothers.”

Most notable, perhaps, is the narrator’s suggestion that for this rather greedy Yankee, the lovely Katrina and her bountiful farm were not enough: “his heart yearned after the damsel who was to inherit these domains, and his imagination expanded with the idea, how they might be readily turned into cash, and the money invested in immense tracts of wild land, and shingle palaces in the wilderness.”  In the years following the Revolution, speculators were investing in and developing vast tracts of land in western New York—and many of these land speculators were from New England.

In contrast to Crane’s unattractive physique and grasping personality, native-born Brom Bones is admired as the strongest guy in town.  If Ichabod is read as a hero (as in many adaptations of this story), then Brom is the villain of the piece, but once we acknowledge Crane’s lack of heroic qualities, we must recognize Brom’s charms:

Among these the most formidable was a burly, roaring, roystering blade, of the name of Abraham, or, according to the Dutch abbreviation, Brom Van Brunt, the hero of the country round, which rang with his feats of strength and hardihood. He was broad-shouldered and double-jointed, with short curly black hair, and a bluff, but not unpleasant countenance, having a mingled air of fun and arrogance. From his Herculean frame and great powers of limb, he had received the nickname of BROM BONES, by which he was universally known.

I would argue that Ichabod Crane is neither a New Yorker nor a hero; he represents the pushy New Englanders who were moving into New York at a rapid pace, often resented by the earlier colonists.  Brom, on the other hand, is attractive and strong, if arrogant, and pride has never been a trait that New Yorkers lacked or for which they apologized.

The climax of the tale takes place when Crane, rejected by Katrina after a country dance, mounts a borrowed horse to make his way back home.  The thoroughly frightened Crane then meets a gigantic, silent, headless horseman who chases him through the countryside, over a bridge, and into the churchyard where, instead of vanishing as Ichabod had hoped, the apparition flings his head at the schoolteacher, knocking him off his horse.  The next day, the horse was found without a saddle, and Ichabod’s hat near a smashed pumpkin, but Crane himself had disappeared without a word or a trace.

After Crane’s ignominious disappearance, Brom Bones wins Katrina; the story’s narrator notes that Brom “was observed to look exceedingly knowing whenever the story of Ichabod was related, and always burst into a hearty laugh at the mention of the pumpkin; which led some to suspect that he knew more about the matter than he chose to tell.”  Like a real New Yorker, Brom runs his rival out of town.

It seems extraordinary that Irving’s tales and characters retain their iconic status today.  Is it possible to think of any other fictional literary characters invented more than a hundred years ago who remain equally familiar to new generations of Americans?  I would welcome additional nominations as well as your ideas about the ongoing appeal of these New York stories.


Washington Irving’s Sunnyside; http://www.hudsonvalley.org/historic-sites/washington-irvings-sunnyside

 Rip Van Winkle, A Posthumous Writing of Diedrich Knickerbocker, Washington Irving; http://www.bartleby.com/195/4.html

 The Legend of Sleepy Hollow, Washington Irving; http://www.bartleby.com/310/2/2.html

Leave a Reply

Your email address will not be published. Required fields are marked *