'The Legend of Sleepy Hollow' is a short story written by Washington Irving in 1820. It is related by an unnamed narrator, and is set in rural New York, during the late 1700's. Specifically, in a remote glen called Sleepy Hollow, which is near the Dutch settlement of Tarrytown. It is a place steeped in myth, rife with tales of ghosts and uncanny happenings which fire the imaginations and superstitions of the locals.
The most popular of these stories center around the Headless Horseman, supposedly the ghost of a Hessian soldier who had his head shot off by cannon fire during the revolutionary war. According to local legend, he is frequently seen galloping around at night, looking for his head. Perfectly understandable under the circumstances, I'd say. The narrator introduces us to the local schoolteacher, Ichabod Crane.
Crane is much like his name: tall, skinny, and ungainly. He is not native to the area, being from Connecticut, but has absorbed the local superstitions, which are accentuated by his reading of Cotton Mather's writings. Ichabod's love of ghostly stories is equaled only by a fondness for large, hearty meals which belies his gangly form. He keeps well fed by making the rounds to his students' homes and dining with their families. His favourite place to dine is the home of the Van Tassel's, who are the most prosperous farmers in the area. There is however, another attraction for Ichabod here besides great food: Mr. and Mrs. Van Tassel's only child, eighteen year old Katrina. Crane has a notion to court her; Baltus Van Tassel is a generous, indulgent father, and Ichabod can't help but think that he'd be a generous, indulgent father-in-law as well.
Up until now, the smart money has been on Abraham "Brom Bones" Van Brunt winning Katrina's hand. Renowned throughout the countryside for his great strength, and his skill and agility on horseback, he and his rowdy friends often gallop through the town, whooping it up. Since he is generally good-natured and well-liked, his high jinks are met with rueful smiles rather than anger. When he starts paying court to Katrina, her other suitors back off- until Ichabod Crane.
Besides teaching school, Ichabod also runs the singing school, which Katrina attends. She apparently isn't very good, because Crane finds it necessary to frequently come by the Van Tassel home to give her extra tutelage. Hmm. It's not quite clear how deep Ichabod's affection for Katrina is... it's true that he daydreams about her, but mostly about her preparing delicious meals for him. The more time he spends with her, the less time Brom does, and Van Brunt isn't happy about it. He would like to challenge Crane man-to-man, but Ichabod, well aware that he's no match for Brom physically, is careful never to be caught alone by him. Van Brunt is reduced to playing practical jokes on the nervous school teacher.
Ichabod's matrimonial hopes receive a boost when he gets an invitation to the Van Tassel's harvest party. Dressed in his finest, he borrows a broken down old workhorse so he can ride to the party in style. Once there, Crane eats to his heart's- and stomach's- content, and spends some time swapping ghostly tales with the locals. As Ichabod prides himself in his dancing ability as much as his singing, he also spends a lot of time tripping the light fantastic. As he dances with Katrina, Brom looks on, stewing.
The party is a rousing success- for everyone except maybe Brom- and as it winds down, most of the jolly crowd heads for home. Ichabod, however, lingers. Emboldened by the successes of the evening, he stays behind to speak privately with Katrina Van Tassel. It seems likely that, in high spirits, he pops the question. It's unclear exactly what happens... our unnamed narrator doesn't know precisely... but what he does know is that Ichabod is in no good mood when he leaves the Van Tassels. Whatever his hopes, they have obviously been dashed. Gloomily,Crane mounts his sway-backed steed and heads for home.
As he travels through the dark woods, all the tales that he has read and heard prey on his mind and fray his nerves. Then, just as he reaches a very secluded section of the road, he is unnerved to realize that a dark, cloaked rider is following close behind him. Silently the rider speeds up when Ichabod does, and slows when he does. Ichabod summons the courage to look behind him, and is terrified to see that the rider has no head- and is actually carrying his head on his saddle. His nerve breaking, Crane tries to urge his old horse to a run, desperate to escape from his headless pursuer. Galloping through the Hollow in a blind panic, Ichabod starts across the bridge by the church. Reaching the bridge as well, the dark rider suddenly hurls his head directly at the terrified schoolteacher.
The next morning when Ichabod doesn't show up at the schoolhouse, people go looking for him. They find the old horse wandering around loose, his saddle lying trampled in the road, next to a smashed pumpkin. Ichabod Crane is never seen again, his belongings left unclaimed at the schoolhouse. The superstitious in the community assume that the Headless Horseman got him, which is why he disappeared without a trace. The less credulous, however, note that Brom Bones smirks and looks knowing whenever the matter is brought up. Some years later, a local returns from a travelling and says that he saw Ichabod Crane in Connecticut, where he apparently returned after having his hopes dashed by Katrina Van Tassel, and his courage broken by the Headless Horseman. Our narrator leaves it up to the reader to decide which of the accounts to believe.