The Headless Horseman Pursuing Ichabod Crane (1858) is a painting by American artist John Quidor, depicting a scene from Washington Irving's 1820 short story "The Legend of Sleepy Hollow".

In one hand, the Headless Horseman is holding a pumpkin, which he is preparing to throw at Crane.

The painting is one of several by the artist based on scenes from Irving's written works about Dutch New York, including such paintings as Ichabod Crane Flying from the Headless Horseman (1828, Yale University Art Gallery) and The Return of Rip Van Winkle (1849, National Gallery of Art).

[1][2] Quidor first exhibited the picture at the National Academy of Design in New York City.

[3] The Smithsonian American Art Museum in Washington, D.C. bought the painting in 1994, but it was removed from display in 2021.