Sleepy Hollow (New York) Horsemen

A two-century-old tale comes to life each Friday night during football season in Sleepy Hollow, New York.

Sleepy Hollow High School, located 28 miles north of Manhattan, leans into the village’s fictitious history and features one of the most remarkable mascots in the country.

The school is home to the “Horsemen,” a nod to the 1820 short story “The Legend of Sleepy Hollow” by Washington Irving. While the high school has long held the name Sleepy Hollow, the village name didn’t come into being until 1996, when residents of North Tarrytown voted to change it.

The famous tale centers on Ichabod Crane, a superstitious schoolteacher who encounters a Headless Horseman while riding home one night. The Headless Horseman is the ghost of a Revolutionary War soldier who was decapitated by a cannonball – and rises from the grave to search for his missing head.

At Sleepy Hollow High football games, a real-life Headless Horseman leads the team to the field on the back of a jet-black horse.

Michael Arias, Sleepy Hollow High’s athletic director, works with the football program’s booster club to coordinate the mascot before each home game. Sleepy Hollow has numerous equestrians in town who perform throughout the year, as the village has become a major tourist destination – especially around Halloween.

The Westchester Journal News reported in 2024 that the live mascot tradition began around 2009, and that the mascot is one of the highlights for both home and visiting fans during games outside of the on-field action.

Jordan Morey is manager of communications and media relations at the NFHS.