The Legend of Sleepy Hollow
Adapted by Jonathan Josephson
From Washington Irving’s The Legend of Sleepy Hollow

Washington Irving’s iconic tale of the Headless Horseman of Sleepy Hollow comes to life in this lyrical and literary reimaging of the classic story! Follow the affable schoolteacher Ichabod Crane as he endeavors to conquer his own fears and self-doubt in order to win the heart of the coquettish Katrina Van Tassel. Along the way, he’ll battle Brom Bones – the self-absorbed, self-proclaimed hero of the realm – and of course, the dominant specter of the land: the Headless Horseman of Sleepy Hollow.

Washington Irving (1783-1859) was born on April 30, 1783, in New York City. He began to contribute satirical essays and sketches to New York newspapers as early as 1802. A group of these pieces, written from 1802 to 1803, was collected under the title Letters of Jonathan Oldstyle, Gent.  A History of New York (1809), ostensibly written by Irving’s famous comic creation, the Dutch-American scholar Diedrich Knickerbocker, is generally considered the first important contribution to American comic literature. Under the pen name of Geoffrey Crayon he wrote the essays and short stories collected in the Sketch Book (1820), his most popular work. Two of the stories, “Rip Van Winkle” and “The Legend of Sleepy Hollow,” set in days when New York was a Dutch colony, are classics in American literature. In 1842 he was appointed U.S. minister to Madrid, where he lived until 1846, continuing his historical research and writing. He returned to the U.S. again in 1846, settling at Sunnyside, his country home near Tarrytown, New York. There, as the acknowledged leader of American literature, he remained until his death on November 28, 1859. Among his other works are Bracebridge Hall (1822), Tales of a Traveller (1824), History of Christopher Columbus (1828), A Chronicle of the Conquest of Granada (1829), The Crayon Miscellany (1835), Oliver Goldsmith (1849), and Life of Washington (5 vol., 1855-59).

This adaptation of The Legend of Sleepy Hollow debuted at the first ever Wicked Lit in 2009 at Greystone Mansion. It was subsequently produced as a part of Wicked Lit 2013 at Mountain View Mausoleum and Cemetery, and then a longer version, The Legend(s) of Sleepy Hollow (the known and the true tale of what happened the night Ichabod Crane encountered the Headless Horseman) was produced at Chance Theater in 2015 as part of the company’s inaugural TYA series. Since that time, both plays have been produced dozens of times by theatres and schools around the world including productions in the UK, India, Cameroon, and throughout the US.

Photos: (L-R, top to bottom) Robin Walton, Nick Bradford Slimmer, and Stephanie Wilborn in The Legend(s) of Sleepy Hollow at Chance Theater, 2015.(Photo by Doug Catiller). The cast of The Legend(s) of Sleepy Hollow at California University, Pennsylvania, 2021. Nick Bradford Slimmer, Victoria Rafael, and Robin Walton in The Legend(s) of Sleepy Hollow at Chance Theater, 2015 (Photo by Doug Catiller). Eric Deloretta and Shawn Savage in The Legend of Sleepy Hollow, Wicked Lit 2013, Mountain View Mausoleum (Photo by Daniel Kitayama).