In The Legend Of Sleepy Hollow, Brom Bones (Abraham Brunt) and Ichabod Crane are rivals for the affections of Katrina Van Tassel, the beauteous eighteen year old daughter of a wealthy Dutch farmer, Baltus Van Tassel.
Because Ichabod Crane is such an impressionable and foolish man, Brom Bones decides to use this fact to his advantage. Since Ichabod is too cowardly to physically duel with Brom Bones for Katrina's hand, Bones plays practical jokes on the hapless Crane. He and his roughrider friends smoke out the singing school (where Crane teaches) by stopping up the chimney. They also break into the school at night to ransack the place. Not content with these actions, Brom Bones teaches his 'scoundrel dog' to whine whenever Ichabod is instructing Katrina in her singing lessons.
Besides these practical jokes, Brom decides that he will frighten the arrogant Ichabod with a ghostly disguise. When both are invited to a 'quilting frolic' at the Van Tassel residence, Ichabod gleefully thinks that he is about to succeed in gaining Katrina's hand in marriage.
However, Brom decides to scare Ichabod with his Headless Horseman disguise. This is a clever ploy, coming on the heels of various ghost stories shared with abandon during the party. Ichabod, superstitious and gullibly impressionable as usual, is spooked as he travels home in the dark. He fears the worse when he glimpses what he thinks is a gigantic-sized horseman. What's more, the horseman appears to be headless; instead of his head sitting on his shoulders, it is sitting on the 'pommel of his saddle.'
The Headless Horseman mercilessly chases Ichabod on horseback. At last, when Ichabod thinks he is nearing the church bridge (which he thinks will assure his safety), a glance back reveals not the disappearance of the Horseman in 'a flash of fire and brimstone,' but an unexpected action on the Horseman's part. The Headless Horseman throws his head at Ichabod, which hits the schoolmaster in the head.
The Horseman drives on, and Ichabod is never heard from again. In due time, Brom Bones triumphantly wins Katrina's hand in marriage.