The Legend of Sleepy Hollow's setting is in a small village on the Hudson River known as Greensburgh, or Tarry Town. The main character in the story, is Ichabod Crane. He helped in came about for the purpose of instructing the children of the vicinity. The most important point of the story is when Ichabod receives an invitation to attend a party at the Van Tassel's mansion. Ichabod was very happy that he was invited and decided to wear his best suit and he also wanted to impress Mynheer's daughter, Katrina, so he borrowed a horse from Hans Van Ripper. He danced with her too at the party. At the party his rival, Brom Bones, was full of jealousy when he saw Ichabod dancing with Katrina. After the dance Ichabod was talking about the old times in the war with others. Also, people from Sleepy Hollow were at the party, sharing many legends that they had heard in Sleepy Hollow.
One of the stories was about old Brouwer, and how he met the Headless Horseman when he was coming from Sleepy Hollow. When they came to the bridge that was when the Horseman turned into a skeleton. Then he threw old Brouwer into the brook. Brom Bone also had a story about himself returning one night from a nearby village, he had been overtaken by this "midnight" trooper. The trooper wanted to make an offer to race him for a bowl of punch, and when they got to the church bridge, then the trooper vanished. After all the stories were told, Ichabod couldn't get them out of his mind. After the party, he couldn't stop thinking about the stories and so he passed every place where the story had taken place, just to get home. He came to a tree in the road and there was a brook nearby the tree. He came to stream and tried to make the horse go over the bridge but the horse wouldn't right away. Soon after he regained control of the horse, and crossed the bridge the Headless Horseman through his head at him knocking him off the horse.