This film has the examples of:
- Adaptational Heroism: Katrina is portrayed as an inquisitive idealist rather than a manipulative coquette like in the original story. Brom Bones is also depicted more sympathetically, in sharp contrast to the Adaptational Villainy that he usually receives.
- Bindle Stick: Ichabod comes into town with his possessions in one of these.
- Cat Scare: While he's trying to get to sleep, Ichabod is startled by a cat leaping in the window.
- Comically Missing the Point: Ichabod mentions wanting to visit the Great Wall of China:Katrina: Is it so unusual to have a wall in China?
Ichabod: Well, I suppose it must be.
- Framing Device: The film features fictional historian Diedrich Knickerbocker being told the story in a tavern, which was the part of Irving's Literary Agent Hypothesis in the original story.
- Headless Horseman: Gee, ya think?
- The Mockbuster: Of course, cynics would say that it's not a coincidence that this was released in the same year as the Tim Burton version, and it clearly wasn't done for very much money. Still, some Irving purists like this version because it's so faithful to the source material.
- Old-Fashioned Rowboat Date: Brom and Katrina go on one.
- Real After All: As in the 1980 version, the reveal that Brom Bones was pulling a "Scooby-Doo" Hoax is followed by the appearance of the real Headless Horseman.
- Small Town Boredom: Brom and Katrina both feel this way about Sleepy Hollow. However, he wants to go west to the unsettled Ohio Territory while she wants to visit "civilized" locales like Amsterdam. In the end, it's Katrina who gets her way.
- Truer to the Text: This version sticks pretty close to Irving's original tale compared to the Tim Burton film, managing to stretch it out to feature length without any obvious Adaptation Expansion. Some argue this is actually the film's downfall and that Irving's short story just doesn't have enough material for a feature-length film, something the loose film adaptation by Burton & co didn't suffer from.