Other mistake: After the midwife's son lights the candles, watch closely, as the lamp revolves clockwise, you will see the cutout of the witch on the broom. It shows the witch facing to the right (counter-clockwise), which means that the projection would and should show the witch "flying" backwards. (00:53:00)
Continuity mistake: When Peter Van Garret's son gets his head chopped off Peter Van Garret looks out of the window. In the close-up his mouth opens in a gasp. Then it goes to a long shot showing the son with no head and Peter Van Garret's mouth is suddenly closed and then he gasps again in the exact same way.
Continuity mistake: At the end of the movie, after Ichabod gives the Horseman back his head, he and Katrina are shown standing next to each other, and her hair is completely down around her face. It then goes to a shot of them from behind, watching the Horseman, and her hair is pulled back. Next shot of them from the front, it's all down again.
Continuity mistake: In the scene where Crane and the Headless Horseman are fighting atop the moving carriage, Crane shoots at the horseman, leaving a mark on the roof of the carriage. In the next shots, the mark is gone.
Continuity mistake: When Ichabod is investigating Johnathon Masbeth's death, he notes that the neck wound was cauterized immediately, which explains why there's no signs of bleeding. At the beginning of the movie, when Van Garret is killed by the Horseman, a splash of blood is shown hitting the pumpkin that is used for the scarecrow.
Continuity mistake: In the shot where Baltus Van Tassel is speared through with the fence post at the church, you hear a pane of glass in the window break but you never see the post actually go through the window nor do you see the rope that is tied to it at all in the shot. The post simply "appears" coming out of his chest. (01:17:55)
Continuity mistake: When the widow's body is on the operating table, in the wideshot Ichabod removes the first medical instrument from his bag and is placing it on the table. In the next close-up, as he removes his hands from the instrument we see that it is actually the second instrument he has put down, with the first one right beside it. (00:28:15)
Continuity mistake: At the funeral of Jonathan Masbath, there are many shots between Ichabod, Brom and Katrina. There are a few people between Ichabod, Katrina, and Brom. When Ichabod looks over at the other two, the people are gone. Then when they show another overall view, the people are back.
Continuity mistake: Johnny Depp's character repeatedly plays with a little red bird in a cage toy during the movie. Towards the end, he is riding in a carriage and playing with it. We see a shot from his eye view and the bird is upright, meaning if we were seeing it from the opposite side it would be upside down. But immediately after that, we see a shot facing Ichabod. The bird is upright, not like it should normally be. We then cut directly to another shot of Ichabod's view, the bird is upright yet again! (01:21:55)
Continuity mistake: When Ichabod Crane has arrived at Jonathan Masbath's murder scene, after he has retraced the horseman's steps, he goes to open his bag. Look carefully at his hands. When he goes to open the bag from a wide angle his right hand is on our side of the handle, but when the camera cuts to a close-up, it has instantly jumped to his side of the handle. (00:22:28)
Other mistake: Towards the end of the movie when Ichabod discovers that Peter van Garrett and widow Winship were secretly married, we see the marriage certificate. The bride is shown as Emily Winship (maiden). Surely she should have been described as a widow because a maiden was the term for a woman who had never been married.
Continuity mistake: After the Hessian, carrying Lady Van Tassel on his horse, jumps back into the tree, her hand is prominently displayed sticking out of the roots. Ichabod faints and it cuts to a wide shot of the entire tree. You can see where the Horseman jumped into the tree but Lady Van Tassel's hand is not there.
Revealing mistake: When Brom (disguised as the horseman) throws the jack-o-lantern at Ichabod, there is a shot from Ichabod's perspective showing the jack-o-lantern flying toward him. It jiggles from side to side, revealing it was travelling on a wire.
Continuity mistake: When Ichabod is being told the history of the Horseman, it shows the Horseman meeting the two Van Tassel children. After the Horseman motions for them to stay silent, young Lady Van Tassel raises the branch that she's holding and snaps it in half. Later, when Lady Van Tassel tells Katrina everything, another flashback seen occurs that shows a young Van Tassel simply breaking the branch without raising it first.
Factual error: At the very end of the movie, Ichabod addresses to Young Masbath saying the final line "You'll son find your bearings young Masbath. The Bronx is up, the Battery is down and home is this way." However the Bronx was instituted only in 1898, a century later.
Continuity mistake: At the start of the movie where Ichabod is at the City of New York Municipal Watchhouse there is a medieval device to Ichabod's left, which is open and empty. In the following shot, there is a man standing inside with the doors closed around him.