In Washington Irving's classic short story "The Legend of Sleepy Hollow," Brom Van Brunt, known locally as "Brom Bones" for his imposing physique and legendary strength, tells a story about the Headless Horseman to the superstitious Connecticut schoolmaster Ichabod Crane.

Brom boasts that he met the "Galloping Hessian" late one night on his ride home from a neighboring village. The fearless Brom challenges the headless trooper to a race through the hollow for a bowl of punch. Brom insists that he and his imposing steed, Daredevil, would have won the race, but when they reached the church bridge near the churchyard where the Hessian is said to have been buried, "the Hessian bolted, and vanished in a flash of fire."

Washington Irving later implies in the story that Brom Bones might be the Headless Horseman that Ichabod Crane meet on his way home from the party at the Van Tassel's, where Katrina Van Tassel rejects Ichabod's romantic advances.

Brom Bones . . . was observed to look exceedingly knowing whenever the story of Ichabod was related, and always burst into a hearty laugh at the mention of the pumpkin; which led some to suspect that he knew more about the matter than he chose to tell.

On the night that Ichabod Crane encounters the Headless Horseman, the Horseman is implied to have been Brom Bones in disguise, but Washington Irving doesn't explicitly reveal the true name of the Headless Horseman. In the story, he is identified only as "the Hessian," the "Hessian trooper," or the "Galloping Hessian of the Hollows."

According to the legend, the Headless Horseman was a Hessian soldier serving with the British army who was killed—decapitated by a cannon ball, as the story goes—during the Revolutionary War at the Battle of White Plains, New York, in 1776.

In the Memoirs of Major General William Heath, General Health, who participated in the defense of New York City and in battles at Long Island, Harlem Heights, and White Plains—a little less than ten miles from Sleepy Hollow—notes in his entry for November 1, 1776, "A shot from the American cannon at this place took off the head of a Hessian artillery-man."

An American writer, Christopher Rondina, researched American and German—specifically Hessian—records from the period of the Revolutionary War. In his book Legends of Sleepy Hollow: The Lost History of the Headless Horseman, Rondina claims to have discovered the identity of the Headless Horseman. According to Rondina, the horseman's name is Heinrich Range, a Grenadier in the Hessian regiment of Colonel Johan Rall fighting for the British army.

According to Rondina, Heinrich Range is buried in an unmarked grave in the Old Dutch Church Burying Ground near Sleepy Hollow—which Washington Irving mentions in the story—in a section of the graveyard set aside for enemy soldiers.