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Celebrating the 70th Anniversary of The Legend of Sleepy Hollow

“Gather round friends and hear my tale that started long ago on the Sleepy Hollow Trail. When the air is filled with the chill of Fall, he’s the one who leads them all. From witch’s laughter and ghoulish growls to ghosts and monsters on the prowl. With glowing pumpkin to light the way, he’s lurking to find his perfect prey. He’s the bringer of Halloween fear, beware, the Headless Horseman is here!”





The Adventures of Ichabod and Mr. Toad

The Adventures of Ichabod and Mr. Toad first released on October 5th, 1949. It was the 11thDisney animated movie and consisted of two segments. The first portion of the film was a cartoon of Mr. Toad from the children’s book “The Wind in The Willows.” Many Disney fans will recall the colorful Mr. Toad and the attraction he once had at Walt Disney World. Since we’re in full swing for Halloween season, I’m focusing on the second segment, The Legend of Sleepy Hollow.

The Legend of Sleepy Hollow

The Legend of Sleepy Hollow tells the story of Ichabod Crane and the Headless Horseman. It’s based on Washington Irving’s short story of the same name. Although Sleepy Hollow was first published in 1820 while Irving was traveling abroad in England, the story is set in Tarrytown, New York during 1790.





Recap of Original Story

The story introduces readers to Ichabod Crane, who moves into the New York town to work as a schoolmaster. He quickly becomes rivals with a local town hero, Brom Bones, by competing with him for the hand of a wealthy farmer’s daughter, Katrina Van Tassal. However, Ichabod is a superstitious fellow and Brom uses this to his advantage at a village party by sharing a chilling ghost story of the Headless Horseman. Ichabod leaves the party with superstitious fear wrecking his nerves. He lets his fear overcome him when he comes across the Headless Horseman while journeying home. He races in panic with the ghostly rider in hot pursuit.





The climax of the chase happens on the edge of town at a bridge when the Headless Horseman howls while throwing his pumpkin head at Ichabod Crane. The ending keeps it vague as to whether the Headless Horseman was truly a ghost or Brom Bones in disguise, but readers are assured that Ichabod safely got away and settled down in a different town.

Being a classic American gothic tale, it’s no surprise Walt Disney chose to make an animated adaption of it.

Disney’s Animated Version

The Disney adaption of The Legend of Sleepy Hollow follows the same story as the book. It does have a lighter tone than the original story and has its comedic moments. The legendary Bing Crosby narrated the movie and sang three unique songs for the production. One interesting fact about the animated short is that it was the only time that Bing Crosby ever collaborated with Disney for a project.

Walt Disney was deeply involved with the production of Sleepy Hollow. He wanted to keep the time period historically accurate in regards to the animated depiction of the characters and overall village design. Walt had his “Nine Old Men” assigned to the project. For those unfamiliar, these were the nine legendary animators that Walt Disney used for his classic Disney films. They helped define the standards of Disney animation and laid the cornerstone for future animated films and cartoon shorts. Making the animated short was a labor of love for Bing Crosby, Walt Disney, and the “Nine Old Men.”

Even though it’s been 70 years since its release, The Legend of Sleepy Hollow is still an animated masterpiece and is played each Halloween season as a creepy classic for families to enjoy.

Presence in Disney Parks

There are some tributes to Sleepy Hollow and the Headless Horseman at Walt Disney World. Inside Magic Kingdom you can find Sleepy Hollow Refreshments at Liberty Square. The building and its proximity to a bridge is a direct homage to the film.

The Headless Horseman appears at Mickey’s Not-So-Scary Halloween Party as well. He comes out prior to the parade and gallops down the street while waving his pumpkin head. An interesting note is that he will stop at the bridge near Sleepy Hollow Refreshments. This is in reference to how his spirit is unable to cross the bridge in the film. He will slowly cross before continuing his ride past Cinderella’s Castle and down Main Street. His arrival on the street is a highlight of the night for many who attend the Halloween Party.

In past years, a special “Return to Sleepy Hollow” event was held at Disney’s Fort Wilderness Resort. Visitors were able to watch the animated short near the horse stables and take photos with the Headless Horseman in a special character photo op.

Some merchandise and apparel featuring the Headless Horseman can be typically found each Halloween season at Walt Disney World.

“You Can’t Reason With A Headless Man”

With just a few days to go before Halloween, there’s still time to watch this timeless animated classic. Watching The Legend of Sleepy Hollow is a spooky tradition I intend to keep doing each Halloween season.

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Kevin Koszola

Kevin is an Orlando, FL resident and Disney enthusiast. Other interests include movies, classic rock, sports, comedy, cooking, and enjoying outdoor activities.
Kevin Koszola


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