In New York at the end of the 18th century, the police still used the old way of handling cases, torturing criminals to extract confessions. The young policeman Ichabod Crane (Johnny Depp) believed in the scientific way of handling cases, so he was ostracized by his peers in the city and was sent to a small town called Sleepy Hollow to handle a serial murder case. There has been a legend about the "Headless Horseman" in Sleepy Hollow. It is said that he was a Black Forest mercenary who fought for bloodthirstiness. After being beheaded by the enemy, his lonely soul has been wandering in Sleepy Hollow. On dark and windy nights, he would ride a fast horse and hold a big axe to cut off the heads of pedestrians passing by. Within two months, three people in the town had been killed. Crane lives in the home of the local rich man Fantasso (Michael Gambon). He doesn't take the legend of the "Headless Horseman" seriously, but people die one after another. He also witnessed the "Headless Horseman" chopping off the head of the town sheriff. He has to believe in the existence of the legend and is determined to find out the truth. After some investigation, Crane puts his suspicion on Fantasso. At the same time, his budding love with Fantasso's daughter Katrina (Christina Ricci) is also destroyed by the cruel reality. Just when Crane thought that the truth was revealed and was about to leave Sleepy Hollow in sadness, things took an unexpected turn...