The story of Ichabod Crane and the Headless Horseman, based on Washington Irving's The Legend of Sleepy Hollow (narrated by Bing Crosby). The gangly and lanky Ichabod Crane was the new schoolmaster in Sleepy Hollow. His somewhat odd behavior made him the ridicule of the rambunctious and robust town bully Brom Bones. Despite his odd appearance, Ichabod quickly proved to be a ladies' man charming all the eligible local maidens. Finally, however, Ichabod discovered the town beauty, Katrina Van Tassel. Katrina was the beautiful young daughter of Baltus Van Tassel, the wealthiest farmer in the area, and Brom's intended. Katrina was a coquette by nature but saw Ichabod as an opportunity to break from the monotony of Brom scaring away every other potential suitor. Ichabod had his eye on the Van Tassel wealth and was infatuated by Katrina's beauty and grace as well.
After a number of comically unsuccessful efforts by Brom to dispose of Ichabod, including a scene at the Van Tassel's Halloween party where he tried to switch his short overweight dance partner Tilda with Katrina, the situation changed when Brom decided to take advantage of Ichabod's strong superstitions. Brom musically told the tale of the Headless Horseman to frighten the teacher. That Halloween night, Crane's lonely ride home became exceedingly frightening because of his exposure to the possibility of encountering the ghost. The atmosphere of fear increased in intensity until it broke the tension at a false alarm, whereupon Ichabod and his horse laughed hysterically in relief. Immediately, the true (?) Headless Horseman appeared, laughing maniacally, riding a large black horse that bore a strong resemblance to the one owned by Brom. Then followed a spectacular chase scene wherein the visually impressive Horseman pursued Ichabod with wild abandon, only to be deterred when Ichabod crossed a bridge near the local Dutch graveyard (the bridge being the point beyond which the horseman couldn't go, according to the tale). The Horseman then hurls his own severed head (shown to actually be a fiery Jack-o'-lantern), at Ichabod. The Jack-o'-lantern is seemingly hurled right at the audience, bursts into flames as it collides, and everything fades to black.
The next morning, the only things found by the bridge were a shattered pumpkin and Ichabod's hat. Brom shortly thereafter married Katrina. It was later rumored that Ichabod married a rich, plump widow with many children (who all resemble Ichabod to an amazing degree), in the next county. But the simple, common denizens of Sleepy Hollow firmly denied this; they all knew that Ichabod was spirited away on Halloween Night by the ghoulish Headless Horseman.
- Baltus Van Tassel
- Brom Bones (voiced by Bing Crosby)
- Headless Horseman (voiced by Billy Bletcher)
- Ichabod Crane (voiced by Bing Crosby)
- Ichabod's horse (voiced by Clarence Nash)
- Katrina Van Tassel (voiced by Bea Benaderet)
- Tilda (voiced by Bea Benaderet)
- Walt Disney Mini Classics: The Legend of Sleepy Hollow
- Disney Favorite Stories: The Legend of Sleepy Hollow
- Walt Disney's Fables: Volume 1
- Walt Disney's Fables: Volume 1
- At the time the film was made, the village in which it is set was officially known only as "North Tarrytown"; the community changed its name to "Sleepy Hollow" (which had traditionally designated only the area, not the village itself) only in 1996.
- In their book Disney Animation: The Illusion of Life, Frank Thomas and Ollie Johnston said that some of the studio's animators quit after this. They felt that Walt was too demanding and the animation too stressful during the last segment.
- The Old Dutch Church of Sleepy Hollow makes its appearance only during the narrative introduction to this segment of the film.
- Ichabod's (borrowed) horse is named "Gunpowder" in the original story.
- Bea Benaderet, who voiced Katrina Van Tassel and Tilda, is best known as the voice of Betty Rubble on Hanna-Barbera's The Flintstones. She also played major parts in the 1960s comedies The Beverly Hillbillies (she was Pearl Bodine, Jethro's mother) and Petticoat Junction (she was Kate Bradley, who ran the "Shady Rest" hotel).
- Unlike many Disney adaptations, "The Legend of Sleepy Hollow" makes relatively few changes to the original story (and far fewer than the changes made to The Wind in the Willows, the source of its companion piece); however, some that were made include the following:
- In the original story, "Brom Bones" is only a nickname for Abraham Van Brunt; the film ignores this fact.
- The Headless Horseman in the story is supposed to have been a Hessian (German) soldier who had his head taken off by a cannonball while fighting for the English in the American Revolution; the film leaves all this complicated backstory out.
- The "frolic" in the original story is not stated to take place at Halloween, which was a holiday the Dutch settlers of old New York would probably not have celebrated.
- In the film, it's stated that the Headless Horseman's power ends when "you cross that bridge"; it was actually a common superstition in Irving's time (and long before) that no supernatural being was able to cross over running water.
- Brom Bones would probably never have heard of the "banshees" he sings about in the film: they are an Irish legend and became familiar to most Americans only after the waves of Irish immigration in the 19th century, while the people of Sleepy Hollow were explicitly of Dutch extraction. (Bing Crosby, however, prided himself on his Irish ancestry!)
- Though Brom sings that the Horseman has a "flaming top" and later in the film does in fact have a Jack-o'-Lantern for a head, in the original story no flames or features are mentioned, and the only thing found afterward is a shattered pumpkin, with no mention of any carving or source of light (such as a candle). Disney may, in fact, have been among the first to show the Horseman's "head" as a Jack-o'-lantern rather than as a simple pumpkin. (As late as 1934, Ub Iwerks in an animated short depicted the Horseman with an uncarved pumpkin head.)
- In the movie, Ichabod is still on his horse when he "dies"; in the original story he loses both his borrowed horse and saddle, motivating him to flee from Sleepy Hollow in order to avoid paying for their loss to the ill-tempered owner (and not to face the Headless Horseman again).
- The Headless Horseman is the only Disney Villain to triumph in the end.