Ichabod Crane is a newcomer to the Hudson Valley; unlike the generations of Dutch settlers that have preceded him, he has neither the strength nor the means to become a farmer and landowner. His single marketable skill is teaching, and in the isolated hamlet of Sleepy Hollow this pays meager rewards. His schoolhouse is decrepit, one large room constructed of logs; its broken windows have been patched with the leaves of old copybooks. Ichabod’s quarters are whatever rooms the neighboring Dutch farmers who board him for a week at a time are willing to provide. Ichabod thus makes the rounds of the neighborhood, and his small salary, combined with his constantly changing address, allows him to store all of his personal possessions in a cotton handkerchief.

Because he comes from Connecticut, a state whose major product is country schoolmasters, Ichabod feels both superior to the old Dutch stock of the valley and frustrated by his perpetual state of poverty. He compensates for the former by regularly caning the more obstinate of his little charges and for the latter by doing light work on the neighboring farms. He further supplements his income by serving as the local singing master, instructing the farm children in the singing of psalms. Never missing a chance to curry favor with the local mothers, Ichabod always pets the youngest children “like the lion bold” holding the lamb. In short, his single goal is self-advancement, and though he has merely “tarried” in Sleepy Hollow, he clearly will remain if his prospects improve.

Ichabod cannot rely on his looks or strength to advance him, so he cultivates a circle of farmers’ daughters, particularly those from the more prosperous families, and impresses them with his erudition and vastly superior tastes. He has, indeed, “read several books quite through,” among them Cotton Mather’s account of witchcraft in New England. He believes even the strangest of these tales; indeed, he frightens himself so much when he reads them that he is startled when he hears a bird or sees a firefly. He is, in other words, completely naïve and suggestible. The local tale of the Galloping Hessian who rides headless through the woods of Sleepy Hollow particularly alarms him. A snow-covered bush in the half-light is enough to convince Ichabod that he has seen the headless horseman.

One of Ichabod’s music students is Katrina Van Tassel, the eighteen-year-old daughter of a prosperous Dutch farmer. She is “plump as a partridge; ripe and melting and rosy-cheeked as one of her father’s peaches.” She also, as her father’s only daughter, has “vast expectations.” Though she is also something of a coquette, the prospect of her inheritance makes her seem to Ichabod a desirable bride, and he determines to win her.

Ichabod’s mouth waters when he contemplates the fruits of old Baltus Van Tassel’s land. He dreams of the fat meadowlands, the rich wheatfields, and the rye, buckwheat, fruit, and Indian corn that will be his if he can win Katrina’s hand. Once married to Katrina, he could invest in large tracts of land. He can even imagine Katrina with a whole family of children, setting out with him for promising new territories in Kentucky or Tennessee. It is, however, the sumptuous comfort of the Van Tassel home that makes him realize that he must have Katrina.

Winning Katrina, however, presents a problem in the person of her rugged, rough-edged Dutch boyfriend, Abraham Brunt, nicknamed “Brom Bones” because of his Herculean size and strength. Brom, who has long considered Katrina his, immediately recognizes Ichabod as his rival, and with his gang of roughriders plays a series of practical jokes on the Yankee schoolmaster. However, his pranks—stopping up the singing-school chimney, upsetting the schoolhouse, even training his dog to whine whenever Ichabod sings—do little to thwart the progress that Ichabod believes he is making in his campaign to win Katrina’s hand. Indeed, Ichabod is encouraged when he receives an invitation to a “quilting frolic” at the Van Tassel home.

Ichabod spends extra time dressing and even borrows a horse so that he can arrive in style. The horse, somewhat inappropriately named Gunpowder, is as gaunt and shabby as Ichabod, but this does not prevent him from thinking that Katrina will be impressed. Ichabod continues to imagine the Van Tassel wealth that he will have if he can make Katrina his, and he quickly becomes the center of attention when Katrina dances with him. Brom, meanwhile, looks on with helpless jealousy. Brom enjoys himself only when telling of his close encounter with the headless horseman. Ichabod counters with extracts from Cotton Mather and stories of his own close calls with Connecticut and local ghosts.

An interview between Ichabod and Katrina follows the party, and Ichabod leaves, crestfallen. Could Katrina merely have been trying to make Brom jealous? Ichabod’s anger, frustration, and sudden obliviousness to the rich Van Tassel lands seem to answer this question.

The midnight quiet of the countryside, the gathering clouds, and the ghost stories that Ichabod has heard do not improve Ichabod’s mood. Indeed, he becomes increasingly uneasy as he approaches the tree from which Major Andre had been hanged. Ichabod knows that he will be safe if only he can cross the church bridge, but just then the goblin rider appears on his black horse, closing in fast behind him. Instead of disappearing in a burst of fire and brimstone as he has always been said to do, the rider throws his head at Ichabod. It strikes Ichabod’s own cranium, and the rider passes on like a whirlwind.

Though Ichabod’s borrowed horse reappears the next morning, Ichabod does not. The executor of his estate, Hans Van Ripper, burns Ichabod’s copy of Cotton Mather and the scrawled fragments of a few love poems to Katrina. Ichabod himself becomes part of Sleepy Hollow’s folklore. Some say that he was snatched by the Galloping Hessian, but others say that Ichabod is still alive, that he was afraid to return from fear of the goblin and Hans Van Ripper (from whom he had borrowed the horse) and was mortified by Katrina’s refusal. Brom Bones appears soon after such discussions, always wearing a knowing smile whenever the goblin’s pumpkin head is mentioned.

“The Legend of Sleepy Hollow” represents Irving’s second comic masterpiece, a ghostly tale about things that go bump in the night. The specter in question here is the mysterious Headless Horseman, said to be a Hessian trooper who lost his head in a nearby battle. Each night he roams the countryside in search of it. The unlikely hero in this tale is Ichabod Crane, an itinerant schoolmaster, whose name suits him perfectly: “He 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.”

Irving opens his tale with a marvelous and evocative description of the lush, charming Hudson Valley region of Sleepy Hollow near Tarry Town, the delightful and dreamy atmosphere pervading the place, and the tale of the Hessian trooper’s ghost that supposedly roams near the churchyard. He then introduces the reader to Ichabod, a poor Connecticut Yankee who is very interested in marrying the wealthy, lovely, and flirtatious Katrina Van Tassel, daughter of the richest man in the area.

Ichabod’s plan is to ingratiate himself into her life, winning her hand in marriage. He arranges to teach her psalmody and is therefore permitted to visit Katrina on a regular basis at her family’s prosperous farm. His interest in Katrina, however, is less than honorable. Ichabod wants to acquire her hereditary wealth and sell it off. His chief rival is a brawny local named Brom Bones, who loves Katrina for herself. The two men despise each other; Irving adroitly contrasts Yankee opportunism with Dutch diligence. Ichabod attends a party given by Katrina’s father one night and later, on his way home, meets the terrifying Headless Horseman (Brom Bones in disguise), who drives the superstitious victim out of Sleepy Hollow forever.

Unlike “Rip Van Winkle,” which appears among the first pieces in The Sketch Book, Irving placed “The Legend of Sleepy Hollow” last and followed it in a brief piece summarizing his final thoughts on the book. It, too, is set in the Hudson Valley, but Irving’s point in this tale is markedly different. In “Rip Van Winkle” the old order gives way to the new, but the reverse is true here.

The hypocritical Yankee Ichabod is defeated by the stalwart Dutch Brom, who represents the old order. The contrast between both men could not be greater. Ichabod is a skinny, shrewd, calculating, sterile (and comic) individual, devoid of human affections, who relies on wit in his attempt to defeat his erstwhile rival. He is also a very gullible individual who believes in the supernatural, thus providing his opponent with the weapon that will destroy him. Brom, on the other hand, is a swaggering, athletic type inclined to mischievous pranks, but he does have deep romantic feelings for the beauteous Katrina. Brom is desperate to win her love, but he realizes that he cannot physically challenge his rival to a fight; hence, he devises a stratagem to prey on the schoolmaster’s fear and drive him away from Sleepy Hollow.

Although “The Legend of Sleepy Hollow” is as familiar a tale as “Rip Van Winkle” to generations of schoolchildren, it has not had much success on the stage because of the difficulty of staging the thrilling chase scene at the end between Ichabod and the Headless Horseman. It has, however, been turned into at least three motion pictures. In 1922 the great cowboy humorist Will Rogers starred in a silent-screen version retitled The Headless Horseman. For the second, in 1949, Walt Disney created a full-length animated feature with Bing Crosby as narrator. In 1999 Tim Burton’s version, Sleepy Hollow, made Ichabod Crane into a constable sent to investigate a number of murders attributed to the Headless Horseman. The tale was also made into a television film in 1980.

“The Legend of Sleepy Hollow” is an endearing and charming tale full of good humor, yet it has serious social implications. It questions whether change and progress are better than stability and order. The old virtues of the settlers are more important than those of the destroyers. Irving sides with Katrina, who has rejected Ichabod’s advances, and Brom Bones, who defeats his rival by playing on the hero’s irrational fears. Irving implies that the practical man always will defeat the dreamer. With the creation of “Rip Van Winkle” and “The Legend of Sleepy Hollow,” even if Irving had written nothing else, he would be elevated to literary greatness, because he fashioned two great American myths that perfectly symbolized American ideals and aspirations.