Think Pop Culture Doesn't Matter? Visit Sleepy Hollow, New York


If you’re still operating under the false notion that pop culture doesn’t have a real impact on everyday life, take a look at America’s oldest example, Sleepy Hollow, New York.

When Washington Irving penned The Legend of Sleepy Hollow in 1820 under the pseudonym Geoffrey Crayon, he probably had no idea that his short story would inspire the beloved town of his youth to turn itself into a living homage to his tale. Settled in the late 1600s, the village was originally an agricultural and manufacturing zone of Tarrytown, New York. Nicknamed “Sleeper’s Haven” by early Dutch settlers, Washington Irving picked up on the Anglicized version of the name, “Sleepy Hollow” when staying with family in the area as a boy. Eventually millionaires like John D. Rockefeller would build mansions around the industrial zone that would become known as North Tarrytown at the turn of the 20th century. But it was Irving’s story that proved eternal when, in 1996, the village voted to rename itself Sleepy Hollow.

Street signs are orange and black, as is one of the village’s fire trucks. The Headless Horseman is the school mascot who, dubbed the nation’s “scariest high school mascot”, runs through every football game at half-time. Police cars and fire trucks also bear the Headless Horseman logo with pride. Halloween is celebrated throughout October with haunted hayrides, street festivals, a parade encompassing both Sleepy Hollow and Tarrytown’s main streets, several ghost tours and performances of the Washington Irving legend. The Great Jack O’Lantern blaze puts Christmas light spectaculars to shame and Horseman’s Hollow turns a 17th century Dutch mill into a gory homage to the headless Hessian.

The Old Dutch Church, Ichabod Crane’s presumed safe haven, stands guard over a vast “garden cemetery” designed to allow Victorian families to picnic with their dearly departed. Tours of the cemetery can be taken both day and night and feature stops at the graves of Washington Irving and those who inspired characters in his tale. A fair runs every weekend alongside the cemetery, providing tour groups with the opportunity to walk the grounds with alcohol in hand. The gas station on the other side of the infamous bridge hawks t-shirts and other assorted Headless Horseman souvenirs. And if you’re hungry, there’s always The Horseman Restaurant, a hole in the wall diner that promises you’ll “lose your head” over their milkshakes.

The Legend of Sleepy Hollow was the first piece of American pop culture to make it big on the other side of the pond. In fact, Irving’s short story broke new ground for us roughshod American pioneers, proving to an entire continent of cultural elite that we were just as smart as we were rebellious. Revered as “the first great American author” Irving, schooled as a lawyer, never tried a case. He was able to live off of his income as a writer, which was practically unheard of at the time. Washington Irving was the first American author “… welcomed by noted society and literary figures including actors, writers, artists, Dukes, and Lords, Kings and Queens. Positive reviews were published and Charles DickensSamuel Taylor ColeridgeLord George Gordon Byron, and his friend Sir Walter Scott lauded his humorous and witty style.”

Over the centuries the story’s reputation took on a life of its own, inspiring more than one film adaptation. Disney even issued a spinoff of sorts, pairing Irving’s Ichabod Crane with Mr. Toad of The Wind in the Willows fame for a classic pop culture double feature. The son of a deacon would never think to associate his haunted tale set in the Dutch protestant town with a pagan holiday. Nevertheless, by the mid-20th century, the Autumn fable was tailored to suit the Halloween trend:

Irving makes no mention of Halloween in his tale; rather he set the climax in the evening of a “fine autumnal day.” The ghostly and frightening elements of the tale, however, mean it is now closely associated with the holiday. The link is strengthened by artists who have shown the horseman carrying a scary jack-o-lantern as a head, embellishing what Irving only suggests: that the horseman’s “head” was actually a pumpkin.

Thanks to the wide readership of Irving’s story, now combined with the number of people who know one of the many children’s editions, comic books, animated cartoons, films or television shows inspired by the tale, the characters are well known and easily identified. They have been appropriated and re-imagined, and as a result, have become even further embedded in American popular culture. Through new vehicles and representations, Irving’s tale keeps audiences amused, captivated and terrified after nearly two centuries.


Now, thanks to the new hit TV show Sleepy Hollow, the little village on the Hudson has been remade into quite the bustling town with at least twice as many citizens and a Starbucks (product placement is a powerful thing). You won’t hear the real-life villagers complain, though. Tourism is through the roof. Would Irving mind? Actually, if he were around today, he’d probably be Tweeting about it:

In his time, though, Irving was one of the most famous men in the world. If he were alive today, he’d regularly be featured in gossip magazines—for he was famous not just for his work, but for his personality and for the company he kept.  His life would have been the stuff of an E! True Hollywood Story – for Irving had a knack for going to the most fashionable parties and having the most fashionable friends. And he always seemed to be in the middle of some of the most extraordinary, world-changing events.

Irving’s little story did what American wars, foreign policy and diplomacy simply could not. It built the American reputation on the international scene. Irving charmed his way into the homes and hearts of Europe’s elite and its masses, setting the trend for Kim Kardashian, Justin Bieber, and Hollywood at large. The next time you see Marilyn Monroe on a t-shirt, or Kris Jenner in the newsstands, tip your hat to the Headless Horseman. Better yet, start creating so you can have a real influence on the culture.


Editor’s Note: also check out the previous installments in this year’s Halloween coverage at PJ Lifestyle: 

Ash Freeman: Ranking The Nightmare on Elm Street Films From Best to Worst

Susan L.M. Goldberg: 8 Reasons Why Jews & Christians Should Re-Think Celebrating Halloween

Ash Freeman: Ranking The Friday The 13th Films From Best to Worst

Robert Wargas: Would You Survive a Horror Movie?

Pierre Comtois: The 10 Scariest Movie Monsters of All Time

Jeremy Swindle: The 10 Worst Horror Films on Netflix: Drinking Game Edition