Director Tim Burton included scenes in homage to Disney's animated version of the Sleepy Hollow tale (featured in The Adventures of Ichabod and Mr. Toad (1949)). These include the scene in which Ichabod Crane crosses the covered bridge and hears the frogs underneath croaking "Ichabod" and "Headless Horseman," the following chase sequence where Ichabod is run down and unhorsed, apparently by the Horseman, and the moment in the climactic chase scene in which Ichabod runs into a tree limb, and, thrown through the air, ends up landing on the Horseman's horse backwards.
Historically, Ichabod Crane was a very unattractive man. Johnny Depp wanted to add prosthetics to his face to make himself look ugly, but Tim Burton wanted to base the character on Crane's more unattractive personality traits - his reported squeamishness and eccentricity.
At the start of filming the three-way axe battle with Ray Park, Johnny Depp, and Casper Van Dien, Van Dien broke the index finger of his left hand. Although it was extremely painful, he carried on without telling anyone as he didn't want his part cut short.
A mechanical horse, an updated model of one used in earlier films, was used for studio shots. The mechanical horse was originally developed for riding scenes with Elizabeth Taylor in National Velvet (1944).
In Washington Irving's original story, Ichabod Crane was a school teacher who came to Sleepy Hollow and ran afoul of its resident ghoul, the Headless Horseman. Ichabod was also a teacher in Andrew Kevin Walker's original screenplay for the film, but director Tim Burton brought in Tom Stoppard to re-write and re-structure the screenplay. Burton is a major fan of Mario Bava's Gothic horror films, and, as an homage to Bava's Kill Baby, Kill (1966), Burton adopted the basic plot of Bava picture: a skeptical investigator who places his faith in science and reason treks to an out-of-the-way hamlet plagued by a murderous ghost, only to have his skepticism of the supernatural forcibly broken down by the experience. The film includes numerous visual references to Bava's films, including a scene in which Ichabod dreams of seeing his mother's spike-pierced face after his father killed her - an image drawn from Bava's Black Sunday (1960), a film Burton was once slated to remake.
The town Sleepy Hollow was created from the ground up in three months. At the time of filming, it was the largest set built in England and was put up in record time. The last set that held this record was built for Billy Elliot (2000).
While Tim Burton admired Andrew Kevin Walker's original script, he hired the famed playwright and Academy Award-winning screenwriter Tom Stoppard as script doctor. Stoppard did an uncredited re-write to tone down the violence of Walker's script.
Ichabod Crane faints a total of five times during the movie. He is induced into unconsciousness by Katrina's medicine after his violent meeting with the Horseman. Katrina, by comparison, faints only twice.
The cast and crew often said "The feeling one had walking around Sleepy Hollow's sets, and in particular the town at Lime Tree, was almost as if you were walking around the inside of 'Tim Burton (I)''s head."
This is the first adaption of "The Legend of Sleepy Hollow" that doesn't involve the actor playing the headless horseman having to conceal his head in the cloak, thanks to advancement technology. The head of the actor was covered with a blue mask that was deleted by means of computer graphics. The collar was also created with CGI to match the flow of the robe.
Tim Burton says the movie was inspired by the Gothic horror films of Mario Bava and Hammer Productions. Burton brought a Hammer veteran Michael Gough out of retirement for a small role, and recruited Christopher Lee, a veteran of both Hammer and Bava's pictures, for a cameo.
In The 39 Steps (1935), the professor shoots Hannay in the chest, and it appears that he is dead. However, the bullet was stopped by a hymnbook in the breast pocket of the coat he was wearing. In Sleepy Hollow (1999), Ichabod is shot and saved in a similar manner; this time the bullet lodges in a book of magic spells.