Ichabod Crane is the schoolmaster who arrives in Sleepy Hollow to teach kids at the school. He loves to eat and read a lot. He also teaches women in the chorus where he gets tricked by his rival Brom Bones by making both a dog howl. Soon, Ichabod meets a beautiful girl named Katrina Van Tassel, the daughter of a rich farmer and falls in love with her. One day, Ichabod offers to carry Katrina's groceries home for her but finds that Brom Bones who also has fallen in love with her, sees this, and knocks Ichabod down into the mud and carries Katrina and her groceries home on his horse. However, Ichabod manages to catch up and takes Katrina and her groceries home. When they arrive at Katrina's house, Ichabod kisses Katrina's hand, but just as he's about to leave, Brom shows up. Ichabod runs into Katrina's house and gives her some flowers to which Katrina puts one in Ichabod's shirt pocket. Just as Ichabod is about to leave again, Brom grabs him and is about to hit him, but Katrina manages to distract Brom by waving at him, and Ichabod escapes happily dancing and playing around on his way home.
Soon, Katrina's father is having a Halloween party to which Ichabod attends with a horse that he has borrowed to travel on. At the party, Ichabod dances with Katrina, and as Brom tries to steal her away from him, Ichabod manages to get Katrina back and steals the whole dance floor with her causing everyone to clap for them at the end, much to Brom's jealousy. Later on at the party, Brom, taking advantage of Ichabod's naiveté, tells a scary story about a Headless Horseman who rides every Halloween night in the Sleepy Hollow forest looking for a new head. The story frightens Ichabod so much that he manages to put too much red hot pepper on his egg without realizing it, causing his eyes to begin to water really badly and smoke to come out.
That night, as Ichabod rides home through Sleepy Hollow, he is haunted by Brom's story and hears animals such as frogs, crows, and owls screaming, "Headless Horseman! Headless Horseman! Headless Horseman! Turn back! Turn back! Beware! Beware! Beware!" Soon, Ichabod hears hooves approaching and realizes that it's not his horse, which has stopped dead in his tracks. Ichabod wonders if someone is following them and tries to get his horse to move, but now soon learns that the sound wasn't hooves, but cattails beating on a log. He and his horse start to laugh until they hear someone else laugh. Then, they turn to see that it's none other than the Headless Horseman himself with a sword in one hand and a burning pumpkin in the other. Ichabod gets on his horse, and they ride away with the Headless Horseman chasing them.
Soon, Ichabod sees the bridge that Brom said, "Once you cross that bridge, my friends, the ghost is through, his power ends." Ichabod urges his horse to run towards the bridge but ends up getting his horse accidentally turned around, then runs back into the direction of the Headless Horseman where Ichabod sees that the evil Horseman really doesn't have a head. Ichabod and his horse run once again with the Headless Horseman chasing them, but finally make it across the bridge where Ichabod looks back to see if he is safe and screams as the Headless Horseman throws his pumpkin at him. The schoolteacher tries to dodge the terrible missile by ducking but is too late when it hits him with a tremendous crash and explodes.
The next day, Ichabod's hat is found next to a shattered pumpkin, since that is the only trace of Ichabod himself. Shortly afterward, Brom Bones marries Katrina. Rumors begin to spread that Ichabod is still alive and married to a wealthy widow in a distant county with seven kids looking like him, though some of the people of Sleepy Hollow don't believe the rumors and some do believe them since they say that he must have been spirited away by the Headless Horseman.
Ichabod Crane appears as one of the guests in House of Mouse.
In the beginning of "Halloween with Hades", Mickey tosses a Jack-O-Lantern towards Ichabod Crane who is shaking (since he's seated with the Headless Horseman and his pumpkin head). The pumpkin lands on Ichabod's head, covering it. The Headless Horseman screeches and runs away leaving Ichabod turning his head with a very confused look.
Ichabod made a cameo appearance in "This is Your Life, Donald Duck" of this series along with some other characters.
Ichabod made his first live appearance in 2017, in the Frightfully Fun Parade at Disneyland. He appears in the pre-parade with two Sleepy Hollow "townspeople" being followed closely by the Headless Horseman.
Additionally, a sign hanging outside Ye Olde Christmas Shoppe in Liberty Square at the Magic Kingdom advertising music lessons suggests he may be the proprietor of the Music Shop section of the store.
- Ichabod is very similar to Belle, both love to read and are considered "strange" in their villages but still have admirers.
- Many people believe Ichabod is more of a villain, since he wants Katrina's money and only loves her for her beauty, and some argue that Brom Bones is more of a hero since he doesn't do anything really bad (especially as the Headless Horseman was also implied to have been the real deal and not Bones disguised as him).
- In the original story, the schoolhouse fell into disrepair as Sleepy Hollow could not hire another schoolteacher after Ichabod's disappearance, and some kids believed that Ichabod's ghost haunts it. However, another Sleepy Hollow resident claimed that he happened to see Ichabod alive in New York City, where he got on with his life, getting a job as a lawyer and eventually appointed to the bench as a judge in small claims court.
- During the Headless Horseman scene, Ichabod's screams sound like Pluto, which were provided by Pinto Colvig.