The film was really shot in the Hudson River Valley around Tarrytown, which is where it's meant to take place.
This film has the examples of:
- Adaptation Expansion: The middle of the film is padded out with a new storyline in which Brom Bones frames Ichabod as a "witch-doctor."
- Artistic License History: Ichabod claims that he would have discovered the Earth was round if he lived before Christopher Columbus, repeating the nineteenth-century myth that Medieval Morons believed the Earth to be flat. Incidentally, Ichabod's creator, Washington Irving, played no small part in creating that myth.
- Dunce Cap: Ichabod is shown punishing a student with one of these.
- Headless Horseman: It's right there in the title.
- Love Triangle: As in the original, Ichabod and Brom compete for Katrina's affections.
- Ordered Apology: Brom Bones is ordered to apologize for framing Ichabod as a "witch-doctor." Brom claims a "Just Joking" Justification.
- "Scooby-Doo" Hoax: In this version, it's made explicit that Brom Bones is the Headless Horseman. After Ichabod runs off, there's a shot of Brom throwing off the costume and laughing.
- Tar and Feathers: After becoming convinced that Ichabod is a "witch-doctor," the townsfolk almost do this to him, but at the last minute, it's revealed that he was framed by Brom Bones.
- Think of the Children!: Needless to say, the townsfolk are not happy about having a "witch-doctor" teaching their children.