The Legend of Sleepy Hollow 200th Anniversary 

Westchester County Executive George Latimer (L) and Sleepy Hollow Mayor Ken Wray are joined by the Headless Horseman himself at The Old Dutch Church of Sleepy Hollow to kick-off an 18-month celebration of the Legend of Sleepy Hollow Bicentennial.

It’s going to be the biggest, brightest, lengthiest local celebration Westchester has seen in a very long while, and you’re invited. 

Starting with the Sleepy Hollow Lit Fest on May 18, the villages of Sleepy Hollow, Tarrytown and Irvington are launching an eighteen-month series of events called The Legend Bicentennial, aka the two-hundredth birthday of the publication of Washington Irving’s story collection The Sketch Book of Geoffrey Crayon, Gent., which includes his classic tale “The Legend of Sleepy Hollow.”  

We are proud to kick off the anniversary with a festival that will feature 100 authors signing books and giving presentations. It’s the perfect way to honor an author so ingrained in the cultural landscape of the Hudson Valley,” says Laura Scott Schaefer, of the Lit Fest Steering Committee. 

Another major highlight will be the Sleepy Hollow International Film Festival, from October 10 to 13. “An outstanding celebration of genre cinema in the historic cradle of the American supernatural,” it’s the brainchild of, among others, two locals, Matt Verboy and Dale Cunningham from Somers. The schedule is packed with screenings, competitions, special guests, cast and crew reunions, and showings of Disney’s The Legend of Sleepy Hollow, celebrating its seventieth anniversary, and Tim Burton’s Sleepy Hollow, enjoying a twentieth birthday in 2019. The River Journal is the Official Media Partner of the Film Fest. You can keep up with all the latest developments at 

“We are excited that the first-ever Sleepy Hollow Film Festival will be taking place this fall,” says Village Manager Anthony Giaccio. “The Film Festival, along with our already incredible Halloween season, should no doubt make this year’s festivities the best we’ve ever had.’     

If you prefer live action to celluloid, how about “The Legend of Sleepy Hollow” as a musical? A dramatization, by William Allen Jones, which delivers the famous tale enhanced by rock and pop songs and ballads, is coming to Irvington’s Town Hall Theatre from October 19 to 26. Read more about it at 

But while we enjoy the spooky movies at October’s Film Fest, participate in the county-wide ‘Everybody’s Reading the Legend’ book club, or attend 2020’s academic conference led by Historic Hudson Valley and Irving biographer Andrew Burstein, let’s not forget to give a great big “thank you” to Irving himself, the American innovator who loved our valley best and put Sleepy Hollow on the map.  

Not only did he immortalize the village, “Irving recreated Sleepy Hollow as he had once observed it, acknowledging his debt to the original. The Sleepy Hollow and Tarrytown of the story are artistic representations of the real, post-revolutionary, Dutch-American community of Irving’s youth,” says village historian Henry Steiner. But the author also enriched it for future generations. Our community’s annual celebration of Halloween owes everything to Irving, Ichabod Crane and the Headless Horseman. 

It was while visiting Tarrytown as a teenager in the late 1790’s, and exploring the slow, possibly enchanted farming community of Sleepy Hollow, that Irving came across a version of the local myth: “The apparition of a figure on horseback, without a head. It is said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannon-ball, in some nameless battle during the Revolutionary War.” 

Decades later, jobless, short of funds and living in London, Irving included the legend in his book The Sketchbook of Geoffrey Crayon, Gent., a collection of 34 essays and stories that also contained another immortal tale, “Rip Van Winkle. Suddenly, Irving found himself a critical success and one of the founding fathers of American literature.  

“’Sleepy Hollow’ has become shorthand for all things supernatural,” comments Dr. Elizabeth Bradley, Vice President of Programs and Engagement at Historic Hudson Valley.  

“Irving was America’s first popular writer and his books included massive biographies of Christopher Columbus, the prophet Mohammed, and George Washington, as well as sketches of life on the American frontier and in merry old England. This catalogue of titles comes as a surprise to twenty-first-century readers, who know him largely for the fantastical tales contained in one of his earliest works.” 

Gifted across a wide literary spectrum, Irving was a true trailblazer. He is credited with inventing the short story itself, and his writing laid the foundations for American gothic and romantic genres. His ideas and names became woven into the fabric of our lives (click HERE). 

But Irving was not done with the Hudson Valley. He made his home at Sunnyside: “My heart dwells in that blessed little spot and I really believe that when I die, I shall haunt it; but it will be as a good spirit, that no one need be afraid of.” 

Generous to the end, that’s exactly what he’s done. 

Leave a Reply

Your email address will not be published. Required fields are marked *

Recommended For You

About the Author: Elsbeth Lindner