Sleepy Hollow, New Netherland

From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by name of Sleepy Hollow … A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.

— Washington Irving, The Legend of Sleepy Hollow

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The Native American Mohicans, lived in the area prior to European settlement. They fished the River for shad, oysters and other shellfish. Their principal settlement was called Alipconk, or the “Place of Elms”. The first European settlers of Sleepy Hollow were Dutch farmers, fur trappers, and fishermen. It sits within the lands of the Dutch Colony of New Netherland.

Sleepy Hollow is renowned for its ghosts and the haunting atmosphere that pervades the imaginations of its inhabitants and visitors. Some residents say this town was bewitched during the early days of the Dutch settlement. Other residents say an old Native American chief, the wizard of his tribe, held his powwows here before the country was discovered by Master Hendrick Hudson. The most infamous spectre in the Hollow is the Headless Horseman, the ghost of a Hessian trooper who had his head shot off by a stray cannonball during “some nameless battle”, and who “rides forth to the scene of battle in nightly quest of his head”.

The “Legend” relates the tale of Ichabod Crane, a lean, lanky and extremely superstitious schoolmaster from England, who competes with Abraham “Brom Bones” Van Brunt, the town rowdy, for the hand of 18-year-old Katrina Van Tassel, the daughter and sole child of a wealthy farmer, Baltus Van Tassel. Crane, an outsider, sees marriage to Katrina as a means of procuring Van Tassel’s extravagant wealth. Bones, the local hero, vies with Ichabod for Katrina’s hand, playing a series of pranks on the jittery schoolmaster, and the fate of Sleepy Hollow’s fortune weighs in the balance for some time. The tension between the three is soon brought to a head. On a placid autumn night, the ambitious Crane attends a harvest party at the Van Tassels’ homestead. He dances, partakes in the feast, and listens to ghostly legends told by Brom and the locals, but his true aim is to propose to Katrina after the guests leave. His intentions, however, are ill-fated. After having failed to secure Katrina’s hand, Ichabod rides home “heavy-hearted and crestfallen” through the woods between Van Tassel’s farmstead and the Sleepy Hollow settlement. As he passes several purportedly haunted spots, his active imagination is engorged by the ghost stories told at Baltus’ harvest party. After nervously passing under a lightning-stricken tulip tree purportedly haunted by the ghost of a spy Major André, Ichabod encounters a cloaked rider at an intersection in a menacing swamp. Unsettled by his fellow traveler’s eerie size and silence, the teacher is horrified to discover that his companion’s head is not on his shoulders, but on his saddle. In a frenzied race to the bridge adjacent to the Old Dutch Burying Ground, where the Hessian is said to “vanish, according to rule, in a flash of fire and brimstone” upon crossing it, Ichabod rides for his life, desperately goading his temperamental plow horse down the Hollow. However, to the pedagogue’s horror, the ghoul clambers over the bridge, rears his horse, and hurls his severed head into Ichabod’s terrified face. The next morning, Ichabod has mysteriously disappeared from town, leaving Katrina to marry Brom Bones. Old Dutch wives continue to promote the belief that Ichabod was “spirited away by supernatural means,” and a legend develops around his disappearance and sightings of his melancholy spirit.