“Rip van Winkle” begins with a description setting the scene between the Hudson River and the Catskill Mountains (“these fairy mountains,” which Irving so loved), then introduces us to the protagonist. Rip is a descendant of the Van Winkles who fought bravely under Peter Stuyvesant, though he himself is too timid to participate in such martial gallantry. He is “a simple, good-natured man … a kind neighbor, and an obedient, hen-pecked husband.” Too lazy to work the farm he inherited, he allows it to deteriorate while his children run around in rags. His only pleasures are squirrel-shooting, fishing, and hanging out in the local tavern, but even these activities are curtailed by his “termagant” wife, who torments him with scoldings. He has no option but to get away from her by wandering through the woods with his trusty dog Wolf.
One day, after taking a nap in the forest, he comes upon a group of men who are strangely dressed in old-fashioned Dutch outfits and playing ninepins. They offer him some of their liquor, which puts him into a deep sleep. When he awakens, his dog is gone and his trusty musket has rusted. He wanders into his old Dutch village, only to find it much changed. No one seems to recognize him, nor are any of his old friends around.
Rip’s main role now is oral historian, telling his story along with “a chronicle of the old times ‘before the war’” to all who will listen.
When he asks about them, he learns that they died long ago. In fact, twenty years have passed while he slept, and during that time the American Revolution was fought and the colonists were freed from British rule. The old tavern sign, which used to feature a portrait of King George III, now sports the image of another George—George Washington. The disputatious “tavern politicians” demand to know on which side Rip voted, “Federal or Democrat,” and he naively confesses that he is a “loyal subject of the king, God bless him!”
Naturally, they accuse him of being a Tory and a spy, but in time they accept his story that he has simply been asleep. Unsure who he is anymore, Rip learns to his great relief that his wife has died and he is now as free of that “petticoat government” as the American provinces liberated from their British despots. He is taken in by his daughter and lives out his last years as a contented man and “one of the patriarchs of the village.”
There’s that word again, “patriarch.” As in The History of New York, the Dutch patriarchs are invariably idle and quiescent. Rip’s main role now is oral historian, telling his story along with “a chronicle of the old times ‘before the war’” to all who will listen. That this ordinary man, this “loser,” as one of our presidents is fond of saying, should triumph and ultimately become one of the immortal figures of our culture merely by taking a long nap tells us something about Americans’ apparently unconscious hunger for resisting the heroic.
Steven Blakemore has argued in his thoughtful paper “Family Resemblance: The Text and Contexts of ‘Rip Van Winkle,’” that there is also a political dimension to the tale. A number of pasts—Dutch, Puritan English, and revolutionary era—have been subsumed in the telling, and the changes Rip finds on returning to his village suggest Irving’s own ambivalence about the direction the United States was taking.
The hero, or antihero, of the story is Ichabod Crane, a rather ridiculous-looking schoolmaster who has set his cap for Katrina Van Tassel, the beautiful, coquettish daughter of a wealthy Dutch farmer.
Although, noting a “covert resemblance” between the two Georges, the king and Washington, Irving may also be suggesting that, in a sense, nothing has changed. All this may be true, but it is not why I keep going back to this tale. Long after I’ve absorbed the seriocomedy of Rip’s long sleep and return to reality, I am charmed by the storyteller’s fluency, his controlled irony, his combination of briskness and leisurely relaxation as he pauses to tell us yet another fresh detail of environment and identity.
Irving tells us that “The Legend of Sleepy Hollow” was also in the papers found by the late Diedrich Knickerbocker. The tale begins with a tribute to the Tarrytown and Sleepy Hollow area hard by the Hudson River. “If ever I should wish for a retreat,” Irving says, “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.” In fact, this area is precisely where he would later build his house, Sunnyside. Irving then alerts us to the prevalence of bewitchment in the region, setting us up for the Gothic tale to follow. “Certain it is, the place still continues under the sway of some witching power. … The whole neighborhood abounds with local tales, haunted spots, and twilight superstitions.”
The hero, or antihero, of the story is Ichabod Crane, a rather ridiculous-looking schoolmaster who has set his cap for Katrina Van Tassel, the beautiful, coquettish daughter of a wealthy Dutch farmer. That Ichabod’s favorite book is Cotton Mather’s History of New England Witchcraft shows him to be “an odd mixture of small shrewdness and simple credulity.” (Irving himself had a thorough dislike of Puritanism.)
Ichabod is also a glutton, and he can hardly contain himself when he contemplates not only the fine figure of Katrina but all the food he would be able to eat as her husband. Employing a method of comic elaboration such as Charles Lamb might use, Irving develops it to a high pitch in this story’s prose:
The pedagogue’s mouth watered, as he looked upon this sumptuous promise of luxurious winter fare. In his devouring mind’s eye, he pictured to himself every roasting pig running about with a pudding in his belly, and an apple in his mouth; the pigeons were snugly put to bed in a comfortable pie, and tucked in with a coverlet of crust; the geese were swimming in their own gravy; and the ducks pairing cozily in dishes, like snug married couples, with a decent competency of onion sauce; in the porkers he saw carved out the future sleek side of bacon, and juicy roasting ham; not a turkey, but he beheld daintily trussed up, with its gizzard under its wing, and, peradventure, a necklace of savoury sausages; and even bright chanticleer himself lay sprawling on his back, in a side dish, with uplifted claws, as if craving that quarter, which his chivalrous spirit disdained to ask while living.
Ichabod has a certain courting advantage in that, as a schoolmaster and singing master, he is regarded by the villagers as a gentleman of cultivation: “Our man of letters, therefore, was peculiarly happy in the smiles of all the country damsels.” (Was Irving referring to his own experience?)
His main problem in winning Katrina is the presence of rivals for her hand, especially the brawny, Herculean Brom Van Brunt, known as Brom Bones. Ichabod does what he can to spiff himself up, even borrowing a horse, an old nag, to ride to the shindig to which he and Brom have been invited. The author interjects: “I confess not to know how women’s hearts are wooed and won. To me they have always been matters of riddle and admiration. Some seem to have but one vulnerable point, or door of access; while others have a thousand avenues, and may be captured in a thousand different ways.” Alas, nothing Ichabod tries succeeds; Katrina turns him down, and he leaves the party dejected.
Beyond supplying readymade plots, these oral traditions were ready to hand in his efforts to establish an American literature, one absent all the rich history and defined class structure of England.
At this point occurs the climax of the tale, Ichabod’s encounter with the headless horseman, whom the reader assumes is Brom Bones playing a mischievous trick on him. Ichabod tries to outrun the ghost, but he is hit in the head with a pumpkin and thrown off his horse. After that he disappears, never to be seen in the village again.
The old women in the village assume that he has been “spirited away by supernatural means. … As he was a bachelor, and in nobody’s debt, nobody troubled his head any more about him, the school was removed to a different quarter of the hollow, and another pedagogue reigned in his stead.” Irving has managed to make us laugh at Ichabod while sympathizing with and rooting for him—perhaps because many readers identify with the hapless Ichabod more than the strongman Brom.
In a postscript we are told that a listener challenged the storyteller to supply the moral of the tale and expressed doubts about its veracity. “Faith, sir,” replied the storyteller, “as to that matter, I don’t believe one half of it myself.” Thus Irving manages to have his cake and eat it too, by insisting on the tale’s authenticity while asserting his own skepticism. Is this what might be called postmodernism avant la lettre? In any case, one would never expect such a conclusion to a story by Edgar Allan Poe, whose oeuvre was too invested in readers’ suspension of disbelief to risk disturbing it.
Both of these tales were derived from the folk legends and mythologies involving witches and ghosts that were still prevalent along the Hudson Valley. Though Irving didn’t believe in the supernatural, he found all this material refreshing. Beyond supplying readymade plots, these oral traditions were ready to hand in his efforts to establish an American literature, one absent all the rich history and defined class structure of England. (This was less of a problem for Hawthorne, who solved it by going back to the Puritans and the Salem witch trials.) Longfellow did the same by borrowing from American Indian legends in Hiawatha.
The nineteenth century saw authors in other countries (Germany, Ireland, Italy, Scotland, Norway) attempting to firm up their nationalist claims by ransacking popular ballads, rustic legends, and oral traditions. Idealizing the “common folk” of preliterate cultures was part and parcel of the Romantics’ emotional rebellion against the sophisticated rationalism of Samuel Johnson, David Hume, and Alexander Pope.
Walter Scott (whom Robert Louis Stevenson called “the king of the romantics”) told Irving at Abbotsford, “I don’t choose to contradict the tale … for I am willing to have my lake stocked with any fish, flesh, or fowl that my neighbors think proper to put in it; and these old wives’ fables are a kind of property in Scotland that belong to the estates and go with the soil. Our streams and lochs are like the rivers and pools in Germany, that have all their Wasser Nixe, or water witches, and I have a fancy for these kind of amphibious bogles and hobgoblins.” Soon after Scott also urged Irving to familiarize himself with German folktales, of which he had a large library, Irving tried to teach himself German in order to do so.
“The Legend of Sleepy Hollow” contains much lush, elaborately beautiful writing, many heightened nature descriptions, and a comic irony that percolates through every sentence. It is almost a shame that the climactic image of the headless horseman is what most of us remember, since there is also so much extraordinary wit and description along the way.
“His stories of Rip Van Winkle and Sleepy Hollow are perhaps the finest pieces of original fictitious writing that this century has produced next to the work of Scott,” said Chambers’s Cyclopaedia of English Literature. Remember, the century was still young when the anonymous critic made that judgment; he can be forgiven for not anticipating the wonders of Dickens, the Brontës, William Thackeray, George Eliot, Robert Louis Stevenson, Anthony Trollope, Joseph Conrad, Henry James, and George Gissing.
The critic’s remarks reflected the high esteem in which Irving was held at the time. He has even been credited with founding the American short story (a tribute I would think belongs more appropriately to Nathaniel Hawthorne). It must have galled Irving to be praised always for those two gems, each of which he wrote almost automatically, in one or two sittings. He was never able to duplicate that happily inspired, imaginative turn as a fiction writer, though he did insert stories as a device to vary his essay collections.
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From A Washington Irving Sketch Book: Reflections on an American Writer. Used with the permission of the publisher, Princeton University Press. Copyright © 2026 by Phillip Lopate
