The Legend of Sleepy Hollow is an 1820 short story by Washington Irving from his collection The Sketch Book of Geoffrey Crayon. It tells the story of schoolteacher Ichabod Crane who competes for the hand of wealthy Katrina Van Tassel. After leaving a party, he is pursued by the Headless Horseman and goes missing from town thereafter.
- Ernie and Bert dress up as the Headless Horseman in a 1997 Sesame Street book, Pumpkin Patch Party.
- The Fall 1983 issue of Muppet Magazine features a picture game in which the reader finds seventeen scary characters. The Headless Horseman can be seen outside the window of the haunted house.