The Headless Horseman is a fictional character that appears in many venues.

Headless Horseman may also refer to:

• Headless Horseman ("Legend of Sleepy Hollow"), a character in the 1820 short story "The Legend of Sleepy Hollow" by Washington Irving

• The Headless Horseman (1922 film), a horror film starring Will Rogers
• "The Headless Horseman" (1934 film), a film directed by Ub Iwerks and part of the ComiColor cartoon series
• The Headless Horseman (1972 film), a 1972 Soviet Western by Vladimir Vajnshtok
• Headless Horseman (film), a 2007 film that aired on the Sci Fi Channel
• The Headless Horseman, a character in the 1949 animated film The Adventures of Ichabod and Mr. Toad
• The Headless Horseman, a character in the 1999 horror film Sleepy Hollow
• Headless Horseman, a 2022 The Asylum film

• The Headless Horseman, a 2002 album by Pegazus
• "The Headless Horseman", a 1949 song from The Adventures of Ichabod and Mr. Toad
• "The Headless Horseman", a 1986 song by Joe Satriani from Not of This Earth
• "Headless Horseman", a 2003 song by Pigmy Love Circus from The Power of Beef
• "Headless Horseman", a 2001 song by the Microphones from The Glow Pt. 2

• The Headless Horseman (novel), an 1865 novel by Mayne Reid
• Headless Horseman Hayrides, a Halloween attraction in Ulster Park, New York
• The Horseless Headless Horsemann, a character in Team Fortress 2

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• All pages with titles beginning with Headless Horseman
• All pages with titles containing Headless Horseman
• Horseman (disambiguation)

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