The Legend of Sleepy Hollow Study Guide

Washington Irving was a fiction writer, biographer, historian, essayist, and US ambassador who worked during the first half of the 19th century. “The Legend of Sleepy Hollow,” along with “Rip Van Winkle,” are the short stories for which Irving is best known. Irving was born in New York and was named after General George Washington (who hadn’t yet been elected President at the time of Irving’s birth, as the Constitution had not been either written or ratified by 1783). Irving studied law before becoming interested in historical writing and short fiction. His writing eventually earned him fame and status, and he was one of the first American authors whose writings received international recognition. He spent 17 years living in Europe (primarily Britain and Spain) and was well regarded abroad. Later in his life he moved back to Tarrytown, New York, and lived on an estate he named “Sunnyside.” He left this estate to serve as the US ambassador to Spain for four years before returning. He continued writing and keeping up with correspondence until his death in 1859.

The “Legend of Sleepy Hollow” takes place around 1790. It’s been fourteen years since the Declaration of Independence, but only seven since the Treaty of Paris officially ended the Revolutionary War. The war is still remembered vividly in Tarry Town, and many of the ghost stories related by the inhabitants recall the very real horrors of war that they so recently witnessed. In 1789, the new Constitution replaced the far weaker Articles of Confederation and created a stronger, more cohesive federal government, with George Washington as the first President. Nevertheless, the United States, over the next several decades, still struggled to create a national sentiment and history—indeed, citizens were far more likely to feel like a resident of Tarry Town or New York rather than an “American.” “Sleepy Hollow” draws on this rich local history, but in doing so, it helps to forge a national tradition as well.

“The Legend of Sleepy Hollow” is one of the stories printed in The Sketchbook of Geoffrey Crayon, Gent., a collection of stories published while Irving was living in England. While most of these stories deal with an American’s perspective on English life, both “Sleepy Hollow” and “Rip Van Winkle” established Irving’s reputation as the first professional American writer. Nevertheless, both these tales are heavily influenced by Dutch and German folktales. Some scholars have noted that “Sleepy Hollow,” in particular, has much in common with the stories collected by German writer and academic Karl Musäus (who was going around collecting old folktales around the same time as the much more famous Grimm brothers). “Sleepy Hollow” was revolutionary because it suggested that the newly formed United States did, indeed, have a history, both literary and cultural—even if this history had much of its roots elsewhere. While it is a horror story, it is also ironic and even funny. Together with Irving’s emphasis on individualism over industry and communality in an increasingly industrialized nation, these traits would come to heavily influence other Americans writing in the Romantic and Gothic traditions. Nathaniel Hawthorne and Edgar Allan Poe are just two authors whose stories recall Irving’s stylistic and thematic modes.