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Irving’s description of Tarrytown as an early Dutch settlement and farming town located on the banks of the Hudson River is historically accurate. Tarrytown is a real place in New York’s lower Hudson Valley, and the first Europeans to settle in the region were Dutch farmers, fur trappers, and fisherman, around the year 1645. When the story begins, around 1790, the town would have already had approximately 150 years of history. For Irving’s European readers, this would not have been considered a long time, but in America it would be considered an old and established town. Irving treats the topic with tongue-in-cheek humor, referring to the first Dutch people to visit the region as “ancient.” This method is effective as it endears him to his American readers and entertains his European readers, which is Irving’s intention all along.

“The Legend of Sleepy Hollow” takes place less than twenty years after the end of the American Revolution. References to the revolution are frequent throughout the story, as many of the older characters participated in the war. Many of the supernatural elements of the story are inspired by real figures and events of the Revolution. The Battle of White Plains was a real battle that would have involved the residents of Tarrytown. General André, whose ghost supposedly haunts a tree in Sleepy Hollow, was a British spy during the American Revolution. He was in fact captured in Tarrytown, although his execution took place in the town of Tappan, not far from Sleepy Hollow, on the other side of the Hudson River. The story’s primary boogeyman, the Headless Horseman, sometimes referred to as the Galloping Hessian, was based on the real Hessian soldiers who fought alongside the British during the American Revolution. Hessia was a German state known for its well-trained army. Members of the Hessian army were professional soldiers, who underwent strict training from a young age and were compensated for their services. Prince Landgraf Friedrich II of Hessia rented these fearsome soldiers out to foreign governments, notably the British. Americans of the time would have been rightly afraid of these highly trained fighters. 

The story was published less than ten years after the war of 1812, a conflict which reignited patriotism and nationalism among the citizens of the young United States. Irving himself served as a military aid during the war. The characters in Sleepy Hollow often exaggerate their role in the American Revolution, evidence that Irving himself both romanticized and respected the struggle for independence. “The Legend of Sleepy Hollow,” along with much of Irving’s other writing, aimed to create a cultural narrative for American history at a time when the United States struggled to be taken seriously as a nation on the world stage.

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