Trivia: Christopher Walken doesn't speak a single word in the entire course of the movie.
Trivia: When Crane starts chopping the Tree of the Dead and he gets blood in his face, this was a joke from the directors as they knew he wasn't expecting the blood. You can see the look of surprise on his face. It was well-known among the cast and crew that Johnny Depp (who played Crane) hated anything being sprayed in his face.
Trivia: Numerous references to other Tim Burton films: a) The dress Katrina Anne Van Tassel wears at the end is similar to Beetlejuice's outfit. b) Crane has various sharp scissor-like tools, which is a reference to Johnny Depp's early film "Edward Scissorhands" (1989). c) The scarecrow at the beginning looks exactly like Jack from "The Nightmare Before Christmas" (1994). d) The covered bridge is a lot like the bridge in "Beetlejuice."
Trivia: Even though Christopher Walken plays the Horseman (when he has his head), Walken did not know how to ride a horse, and as such, a mechanical horse was required for all of his riding shots. This is seen in the "Making Of" on the DVD.
Trivia: Tim Burton, a former Disney animator, makes a few nods to Disney's "The Legend of Sleepy Hollow" in the film. The frog which appears to be croaking Ichabod's name, and Ichabod riding backwards on the Horseman's horse, were both lifted from Disney's short film.
Trivia: In addition to the other two 'Star Wars' links already posted here there's one other one towards the beginning of the film. The judge that orders Ichabod Crane to go to Sleepy Hollow is none other than Count Dooku himself, Christopher Lee.
Trivia: Christopher Walken appears as the Headless Horseman. In The Dead Zone (1983), the last thing Walken's character instructs his school students to read is "The Legend of Sleepy Hollow."
Trivia: Johnny Depp's main inspiration for Ichabod Crane was Richard E. Grant's portrayal of Withnail in "Withnail and I."
Trivia: I recognized the sword twirl that The Horseman does from somewhere, but couldn't place it. Take a look at the credits - one of the actors who plays The Horseman when he's got no head is Ray Park, ie. Darth Maul from Episode 1, who does exactly the same lightsabre twirl once or twice. And another Star Wars link - recognize one of the village elders? Senator Palpatine/The Emperor, no less.
Trivia: Since a blue camera filter was used to make the movie appear darker, the fake blood was actually made as a bright-orange to appear red on film.
Trivia: Sleepy Hollow was the last film in America to be released on LaserDisc.
Trivia: At the end of the film, when Ichabod and the others arrive in New York City, he tells them, "The Bronx is up, and the Battery's down." This is a reference to the song "New York, New York", from the 1940's stage show and movie "On the Town."
Trivia: Despite his prominent billing, Sir Christopher Lee only appears in one scene, which takes place before the opening credits.
Answer: As revealed by Lady Van Tassel to Katrina during the film's climax, the midwife Mrs. Killian was abreast of the secrets regarding the affairs of Peter Van Garrett with the widow Winship, as well as their unborn child. Mrs. Killian revealed this secret to Lady Van Tassel right in front of Mr. Killian, which signed both of their death warrants. However, Lady Van Tassel most likely commanded the Headless Horseman to kill the Killians (as opposed to just saying Mr. & Mrs. Killian), to which the Horseman would instinctively murder their child too. It may have been an oversight on the part of Lady Van Tassel, as the child would undoubtedly be ignorant of affairs and the intricacies of legal matters regarding wills, but then again, she probably didn't care anyway.
Phaneron ★