There’s no feeling quite like the excitement of hearing the “clip clop” of heavy hooves heading down Main Street USA and catching your first glimpse of an imposing black steed whose rider has. no. head.
The Headless Horseman, who leads Mickey’s “Boo to You” Halloween Parade at Disney World and the Frightfully Fun Parade at Disneyland, is a staple of the Halloween season at the Disney parks. One of the highlights for many guests attending Mickey’s Not So Scary Halloween Party or the Oogie Boogie Bash is getting a magic shot with this spooky character in front of the train station.
We love how Disney makes this magical moment look effortlessly spooky! But, of course, a lot of hard work goes in to making sure a headless rider can navigate the parks on horseback. Disneyland did a neat video giving us a behind-the-scenes look at the parade’s most magical moment.
Although all of Disney’s Halloween parties are cancelled this year due to COVID-19, we still wanted our dose of the Headless Horseman! So join us as we shine a spotlight on his hometown of Sleepy Hollow and the spooky legends it spawned!
What is Sleepy Hollow?
Mostly, it’s an invention for tourists!
But, to be more specific, Sleepy Hollow was originally a fictitious town along the Hudson River in New York. Famous early-American author Washington Irving (1783-1859) first traveled “upriver” from his home in Manhattan to escape from an outbreak of yellow fever in the city. He stayed in Tarrytown, New York: a former Dutch settlement steeped in both charming customs and wicked ghost stories.
Of all the scenery of the Hudson, the Kaatskill Mountains had the most witching effect on my boyish imagination
Washington Irving
This witching effect is evident in Irving’s most beloved short stories: “Rip Van Winkle” and “The Legend of Sleepy Hollow.” In these tales, the Dutch culture of the region melds with classic horror anxieties to form some of the first American tall tales.
Washington Irving eventually retired to his beloved village of Tarrytown, where he died and was buried in the cemetery. The town has capitalized on its cameo in “The Legend of Sleepy Hollow” ever since, and in 1996 its name was officially changed to Sleepy Hollow, New York. Sleepy Hollow joins Salem, Massachusetts as the top Halloween tourist destinations in the US, and “haunted Sleepy Hollow” tours are bestsellers during the fall months.
What About Disney’s Sleepy Hollow?
If you’re a Disney fanatic, your first association with the words “Sleepy Hollow” might actually be “funnel cake” instead of “headless horseman!” That’s because one of our favorite quick-service restaurants in Walt Disney World is called Sleepy Hollow Refreshments. Located right on the border between Liberty Square and the castle hub, Sleepy Hollow serves American food and snacks with a delicious Disney twist. Some of our favorites are the Churro Ice Cream Sandwich, the Sweet & Spicy Chicken Waffle Sandwich, and–only during Halloween season–the Pumpkin Spice Mickey Waffle Sundae!
History buffs might notice something besides the cuisine at Sleepy Hollow, though! Disney Imagineers really outdid themselves in the design of the restaurant building itself.
(Right) Disney’s Sleepy Hollow Refreshments
Spot the similarities? The design of Sleepy Hollow Refreshments’ facade is an homage to the house in which Washington Irving retired and eventually died.
Next time you have a craving for funnel cake or Mickey waffles, remember Mr. Irving!
Sleepy Hollow on the Silver Screen
Disney’s earliest associations with the Headless Horseman came during the age of Disney Animation’s anthology films: two or more shorter tales that were collected and premiered in theaters together. 1949 saw the release of Disney’s The Adventures of Ichabod and Mr. Toad, an anthology of two short stories that were…not super related to each other.
But both featurettes had celebrities to draw audiences to the theater: English countryside adventure “Mr. Toad” was narrated by Basil Rathbone (the most famous Sherlock Holmes of the Silver Screen) and “The Legend of Sleepy Hollow” featured narration and original songs by Bing Crosby (of “White Christmas” fame).
Disney Imagineer Mary Blair (who famously designed the “It’s a Small World” artwork) painted the original concept art for ‘The Legend of Sleepy Hollow,” and much of her fantastic color schemes and unique art design remain in the final product.
The plot of the animated featurette “The Legend of Sleepy Hollow” follows the new schoolmaster, Ichabod Crane, who comes to the little village of Sleepy Hollow.
And just beyond, nestled deep in the low rolling hills, a sequestered glen. It’s a quiet, peaceful place, and yet, somehow… foreboding. It abounds in haunted spots, twilight tales and local superstitions.
“The Legend of Sleepy Hollow”
The country hamlet is inhabited by Brom Bones–a Gaston-eque figure who rides a huge black horse up and down the village streets–and the beautiful blonde Katrina Van Tassel. Both these characters’ names and costuming hearken back to the real setting’s Dutch roots!
Awkward and gangly Ichabod, who is inexplicably a ladies’ man, attempts to woo Katrina away from Brom Bones. After quite a few hijinks, it seems as though Ichabod crane will win Katrina’s heart. But Brom has one last trick up his sleeve: a ghost story, which he sings to the guests at the Halloween Ball. I definitely encourage you to watch the video of this scene, sung by Bing Crosby!
Ichabod, it turns out, is extremely superstitious and scared of ghost stories and is terrified of the legend of the Headless Horseman. The song declares that the only way to escape the headless horseman is to cross the bridge out of town, claiming “don’t even try to come up with a plan/you can’t reason with a headless man.”
When Ichabod rides home alone that night, he of course works himself into a terror before encountering a terrifying headless figure riding a huge black charger.
Ichabod narrowly escapes the Headless Horseman by riding over the bridge out of town. Alas: though the rider doesn’t follow him over the bridge, he does throw a flaming jack-o-lantern at the hapless schoolmaster, which strikes him in the head.
Next morning, Ichabod’s hat was found. And close beside it, a shattered pumpkin. But there was no trace of the schoolmaster. It was shortly thereafter that Brom Bones led the fair Katrina to the altar…
The Legend of Sleepy Hollow
The tale ends ambiguously: maybe Ichabod fled to a less-haunted town and married a less sought-after woman. Or maybe, as the Dutch settlers of Sleepy Hollow believed, he was “spirited away by the Headless Horseman.”
This spooky animated flick is a little-known Disney tale that features hijinks, cute songs, and family-friendly Halloween fun! You can find The Adventures of Ichabod and Mr. Toad streaming on Disney+ in their “Halloween” collection. (And if you want more Mr. Toad content, check out The Wind in the Willows or the “Mr. Toad’s Wild Ride” attraction at Disneyland.)
Johnny Depp’s Adventures in Sleepy Hollow
The better-known film adaptation of Washington Irving’s story is 1999’s Sleepy Hollow, directed by Tim Burton and starring Johnny Depp and Christina Ricci. Though Burton would go on to direct Disney’s most famous Halloween flick The Nightmare Before Christmas and Johnny Depp made Jack Sparrow famous for Disney Studios, this version of Sleepy Hollow was a Paramount production and is significantly less family-friendly.
To stretch Irving’s short story into a feature film, Ichabod Crane is turned into a detective and the town of Sleepy Hollow is turned into the scene of a sort of locked-room murder mystery more typical of Edgar Allen Poe than Washington Irving.
I won’t summarize it, but if you can get past this picture of Christopher Walken as the razor-toothed Headless Horseman you can probably stomach this movie.
This movie has everyone: Albus Dumbledore, Captain Jack Sparrow, Wednesday Addams, Vernon Dursley, Rita Skeeter and Saruman (to name a few) so for me it was worth watching just to see if I could spot all the Harry Potter actors.
If you’re interested, Sleepy Hollow (1999) is currently streaming on Netflix US.
So, if you’re looking for a unique DisneyBound or couples’ costume this Halloween, why not try out something from Sleepy Hollow? You can even get a group of friends together and go as Ichabod, Katrina, Brom Bones, the Headless Horseman, or any combo thereof!
If you do wear any Sleepy-Hollow inspired fashion to Disney World, make sure to snap some photos in front of Sleepy Hollow Refreshments (or any of the cute nooks and crannies of Liberty Square for that early-American ambiance! And send them to me on our Facebook or Instagram pages, because I’ve honestly never come across any!
Did you grow up reading or watching “The Legend of Sleepy Hollow?” Have thoughts about Johnny Depp as a steampunk detective? Let me know in the comments below, or on our Facebook, Pinterest, or Instagram pages!
Pixie dust and glamour!
The Fancy Floridian 
