🐴 THE LIGHTER SIDE — Yes, the Headless Horseman leading a high school football team onto the field in Sleepy Hollow, New York is real — and the horse is the star.
At every Sleepy Hollow High home game, a headless rider on a big black horse gallops the team out. Videos of it have racked up millions of views this fall. The rider is Leora Dillon, 56, of Warwick, who rescues and trains horses for a living and works as an ER nurse "to pay for my ponies." Her head hides inside the costume's collar, behind a veil she can barely see through — so she trusts Eagle, a rescue horse who arrived underweight and traumatized in 2017 and now knows the routine cold. "The horse could do it without me," she says. "He's truly the star of the whole thing."
October is her busy season: nearly 200 Horseman appearances booked this month alone.
Source: USA Today (Oct. 29, 2026)
📷 Sleepy Hollow, N.Y. (photo: SteveStrummer / Wikimedia Commons, CC0)
