The Legend Of Sleepy Hollow

The fable of Sleepy Hollow reappears annually around Halloween. Sleepy Hollow is considered one of America's first ghost stories—and one of its scariest. Washington of Irving's 1820 tale of a headless horseman who terrorizes the real-life village. 
Irving didn’t come up with the idea of a headless rider. Legend of headless horsemen can be drawn to the Middle Ages, counting stories from the Brothers Grimm and the Dutch and Irish legend of the “Dullahan” or “Gan Ceann,” a Grim Reaper-like rider who carries his head. A possible origin for Irving’s horseman can be found in Sir Walter Scott’s 1796 The Chase, which is a translation of the German poem The Wild Huntsman by Gottfried Bürger and likely based on Norse mythology. Says a historian at Historic Hudson Valley Elizabeth Bradley
“In 1817 Irving met and became friends with Scott so it's very possible he was affected by his new mentor's work,” says Elizabeth bradley, “The poem is about a devilish hunter who is cursed to be hunted eternally by the devil and the ‘dogs of hell’ as penalty for his crimes.”
Conferring to the New York Historical Society accept Irving was stimulated by “an real Hessian soldier who was beheaded by a cannonball at the time of Battle at White Plains, around Halloween 1776.”
Irving’s story appears in the New York village of Sleepy Hollow, in Westchester County. In it, tall and thin newcomer and schoolmaster Ichabod Crane courts Katrina van Tassel, a young heiress who is also being pursued by the Dutchman Brom Bones. After being ignored by Katrina at a party at the van Tassel farm where ghost stories are shared, Ichabod is chased by a headless horseman (who may or may not be his enemy) who fires a pumpkin at the man, flipping Ichabod from his horse. The schoolmaster vanishes.
Irving moved to the Tarrytown region area in 1798 to flee a yellow fever outbreak in New York City Irving may have drawn inspiration for his story while a teenager in region, according to the New York Historical Society.
“Irving was brought in to local haunted stories and myths at an early learning age,” Bradley says. “He cleverly blends together legitimate locations—the Old Dutch Church and churchyard, ‘Major Andre's Tree,’ some actual family names, containing van Tassel and Ichabod Crane—and a small bit of Revolutionary War history with pure imagery and delusion," Bradley says. "It's a softening plot of a story, and thus completely American.”

By – Abhishek Singh
Content - https://www.history.com/news/legend-sleepy-hollow-headless-horseman