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 Tessel. 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's Fables: Volume 1
- Walt Disney's Fables: Volume 1
- The century that Sleepy Hollow took place in is the 18th Century, the same century as Beauty and the Beast.
- 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 only makes its appearance during the narrating introduction to this animated short.
- This is maybe the only Disney Classic movie to have only one difference with the original story: in the movie, Ichabod is still on his horse when he "died", in the original story he lost the horse and the saddle, motivates him to run away from Sleppy Hollow in order to not paying the loss to the owner (and don't face again the Headless Horseman).
- The Headless Horseman is the only Disney Villain to triumph in the end.