A Look At The Life Of Washington Irving, Sleepy Hollow and The American Short Story

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Washington Irving was America’s first internationally celebrated author and one of New York’s greatest literary figures. Best known for creating “The Legend of Sleepy Hollow” and “Rip Van Winkle,” Irving’s life extended far beyond those classic stories, taking him from New York City to Europe and back again while helping shape American literature during the nation’s formative years.

Photo: By Washington Irving [Public domain], via Wikimedia Commons

Everyone has heard the name Washington Irving, but what about Jonathan Oldstyle or Diedrich Knickerbocker? While Washington Irving was building his literary career, he not only wrote about a wide range of subjects but also used a few entertaining pen names.

When one thinks of Washington Irving, a presumption can be made that he spent his whole life in New York, sleeping under oak trees and trading folk tales with the locals. He did spend special years in New York, but there is so much more to his story.

Born in New York City in 1783, he was named after George Washington, whom he had the pleasure of meeting as a youngster. George Washington would be an important figure in Washington Irving’s life, and Irving would later write one of his best-known biographies, published in five volumes, chronicling the life of the first U.S. president.

Photo: John Wesley Jarvis [Public domain], via Wikimedia Commons

How Irving ended up in Tarrytown, thirty miles north of the city, stemmed from a rather ordinary event. Irving and one of his brothers were sent “upstate” to spend time in the Hastings area with friends when New York City was in the grip of yellow fever. Relatives often sent young family members away from the city to avoid outbreaks of contagious disease. This quiet community where he lodged was full of Dutch settlers with country customs and many unusual legends. Whether Irving knew it or not at the time, he was gathering material for his most famous tale.

New York had more than its share of whispered ghost stories. Because of the real-life bloodshed during the American Revolution and the superstitious attitudes of the time, a spooky tale about a mysterious horseman searching for his missing head appealed to readers. The story of Rip Van Winkle, a man who fell asleep for twenty years while Henry Hudson and his crew bowled in the Catskills, was also included in the same collection. Particularly poignant was the fact that Irving created his colonial “slacker” character Rip Van Winkle and his nagging wife Dame Van Winkle while his family was facing financial ruin.

Washington Irving had relocated to England to help save the family business, but it failed anyway. This desperate situation fueled his literary creativity even further. Curiously titled The Sketch Book of Geoffrey Crayon, Gent., Irving’s collection of stories was published in installments between 1819 and 1820, much in the serialized style later employed by Arthur Conan Doyle and Charles Dickens. Although the family was, as they said at the time, financially “ruined,” Irving had valuable political connections. He was offered a position in the British ministry; however, he instead chose to pursue his dream of becoming a writer. It proved to be a wise decision.

The publisher of The Sketch Book of Geoffrey Crayon, Gent. is credited as C. S. Van Winkle. Washington Irving’s brother Ebenezer, an editor by profession, helped support his brother’s literary ambitions and worked tirelessly to get his work into print. Washington Irving, still living in England at the time, mailed each installment home to his brother for editing. Pamphlets containing the stories, along with essays, drawings, and other literary pieces, circulated throughout the Northeast. Before long, British publishers were reprinting Irving’s work, sometimes with permission and sometimes without it. Having barely passed the bar examination and trained as a lawyer despite disliking formal study, Irving spent much of his later life advocating for stronger copyright protection. He later partnered with publisher George Putnam to better safeguard his literary works.

His travels throughout New York and Europe provided the settings for many of his stories. From the Catskill Mountains, which he visited as an impressionable teenager, to the landscapes of Spain, each destination helped shape his writing. Many admirers of Irving’s work are surprised to learn that he served as United States Minister to Spain from 1842 to 1846. Irving possessed a keen interest in politics, history, and the law, but writing always remained his true calling. He also had a sharp sense of humor, lampooning contemporary New York society in his first full-length work, A History of New York from the Beginning of the World to the End of the Dutch Dynasty, published under the pen name Diedrich Knickerbocker, a playful reference to the knee-length trousers worn by early Dutch settlers. Along the way, he fought during the War of 1812, served as editor of the Analectic Magazine, where he reprinted Francis Scott Key’s poem “The Star-Spangled Banner,” and later served as secretary to the United States Legation in England from 1829 to 1832.

Irving continued writing throughout his life. While some of his later works enjoyed commercial success but received mixed critical reviews, his financial stability finally allowed him to pursue subjects that genuinely interested him, including an extensive biography of the Prophet Mohammed that required years of research. He also encouraged younger writers and contributed to the New York literary magazine The Knickerbocker, named after his famous pseudonym.

After all of his travels and adventures, North Tarrytown became the place where he spent his later years. His home, Sunnyside, served as something of a rural version of the Algonquin Round Table, where artists, writers, and politicians gathered to exchange ideas and nurture their talents. Irving remained there until his death in 1859 and became the area’s most celebrated literary resident. His Legend of Sleepy Hollow evolved into perhaps the quintessential American short story, inspiring the community to adopt the name Sleepy Hollow for its high school and “The Headless Horsemen” as one of its enduring symbols.

During the twentieth century, North Tarrytown became well known for its General Motors assembly plant. After the factory closed in 1996, the community wisely chose to capitalize on Washington Irving’s legacy by officially renaming itself the Village of Sleepy Hollow. The decision proved to be an excellent one, bringing visitors from around the world, especially after Tim Burton’s 1999 film adaptation of Sleepy Hollow renewed interest in Irving’s classic story.

The television series Sleepy Hollow, which premiered in 2013, introduced the tale to another generation of fans. Several cast members visited the village, and portions of the series were filmed nearby. Today, visitors can admire the spectacular autumn foliage while also noticing that the village’s ambulances, police cars, and fire trucks proudly display the Headless Horseman as part of their official insignia.

Photo: Washington Irving and his friends at Sunnyside. According to Princeton University: “Engraving by Thomas Oldham Barlow (1824–1889), after a drawing by Felix Octavius Carr Darley (1822–1888), made from photographs by Mathew B. Brady (1823–1896), in conjunction with an oil painting by Christian Schussele (1824–1879).” [Public domain], via Wikimedia Commons.