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- Ichabod Crane is resurrected and pulled two and a half centuries through time to unravel a mystery that dates all the way back to the founding fathers.
- Ichabod Crane is sent to Sleepy Hollow to investigate the decapitations of three people; the culprit is legendary apparition The Headless Horseman.
- In a small town, a brewing romantic rivalry with a local tough and a school-teacher culminates in a terrifying ride in the night.
- Ichabod Crane, a Yankee wanderer, arrives in Sleepy Hollow and becomes the new schoolmaster. He meets Katrina Van Tassel, and blissfully fantasizes about how he can marry her, ultimately inheriting her father's rich estate. Her suitor Brom Bones, the blacksmith, wants to scare him away and dresses up as the legendary Headless Horseman. During the prank, the real ghost appears and drives Ichabod off.
- Angered that Katrina has grown fond of schoolmaster Crane, Brom Bones determines to scare off the interloper by filling his head with spooky tales of a Headless Horseman. Crane disparages the legends, until one fateful ride home in the dark of night.
- Ichabod Crane arrives in Sleepy Hollow for a fresh start, but his roommate, The Headless Horseman, has different plans for him.
- It's Halloween and friends Nick and Kate are on a mission to find the biggest pumpkin in the patch. Unfortunately, the pumpkin they choose is haunted by the ghost of the Headless Horseman, and he wants his head back.
- 5 teenagers are forced to clean up the woods of Sleepy Hollow, but one by one they are decapitated by a man with a jack-o-lantern mask and a sword, but who could it be?
- It's said "There's no true love without jealousy," yet Henry Taber overstepped the mark in this direction, and, although Tess was the most devoted of wives. Henry saw in every man upon which her glance fell a possible rival. Jack Wilson, the amateur photographer, stopped at their cabin for a glass of water, and merely because Tess hid him a pleasant good day, Henry was vexed. Indeed, that evening when Jack again chanced that way and showed the little wife a few prints of her estate. Henry displayed his displeasure in no uncertain manner, and coax as she would, he refused to come in to supper, but instead sank wearily down on a bench. As he lay there, he beheld his wife come to the door, look cautiously about, and steal softly around the house. Instantly he sprang up and crept after her, until she came to the Big Rock, where he beheld her clasped in the arms of Jack Wilson. The unhappy husband raised his gun and fired, but it was Tess who dropped. So grasping the photographer by the throat he slowly but surely forced him over the cliff. Turning, he found that Tess had staggered off and from his position on the rock he could see her notifying the woodsmen below. Perhaps after all, Jack had been only wounded, but as he climbed down, his worst fears were realized, and he had scarcely time to hide behind the rocks when Tess and the woodsmen appeared. Then commenced a chase up the mountain. At last he reached the top and laid down to rest. Suddenly the woodsmen's heads appeared. Stealthily they crept upon him, while he lay as one petrified, unable to move hand or foot, until the sheriff grasped him firmly by the shoulder. But, as Henry started up, he looked into the pleading face of Tess, again imploring him to come to supper, just as Jack Wilson appeared to get the camera he had forgotten. The man looked around. There stood his cabin. It was only a dream. Gratefully he clasped his wife in his arms, grasped the photographer's hand, insisting upon his sharing their humble evening meal.
- John Carradine narrates the Washington Irving story of Ichabod Crane and the Headless Horseman.
- Sleepy Hollow is the home of America's original horror story: the tale of the headless horseman. But horror doesn't just disappear. Now, filmmakers from the area have tackled the new legends of terror in this iconic area.
- Drift through Sleepy Hollow, the haunted fable town. Experience the uneasy ambience in this slow, quiet, and immersive ride.
- Here is the heart-rending narrative of Ichabod Crane, the schoolmaster of Sleepy Hollow, and his strenuous courtship, the quilting bee, the village dance, the bragging of Ichabod and the true love of Katrina and Brown Bones, and finally the merry prank by which Ichabod is pursued by the Headless Horseman with a pumpkin lantern in his hand.
- this Documentary explores the history of the town of Sleepy Hollow and the story by Washington Irving including the legend of the Headless Horseman
- The fourth of eight short black and white films from director William K.L. Dickson in which he chronicles the story of Rip Van Winkle. In this film, Rip encounters several other dwarf-like mountain-dwellers.
- James Rolfe documents his visit to the village in which Washington Irving based his famous tale "The Legend of Sleepy Hollow" off of.
- In June of 2015, the Sleepy Hollow a wildfire spread under extreme heat and wind conditions into the Broadview Subdivision of Wenatchee, Washington. More than 30 homes and businesses were lost in a two hour period.
- "Welcome to Sleepy Hollow" is a feature length documentary chronicling the 2019 Sleepy Hollow Theatre and Arts Park season in Bismarck, ND. This film showcases their three productions with musical numbers and special behind the scenes footage. We also touch on stories and people from within the walls of Sleepy Hollow.
- A hosted horror movie show with Bryan Hogue as Jack Shadow and Ava Hogue as Aura.
- 1954–19971hUnrated8.7 (58)TV EpisodeFeatures The Legend of Sleepy Hollow (1949), originally from The Adventures of Ichabod and Mr. Toad (1949).
- 1958–196130m7.6 (14)TV Episode
- 1986–2010TV-PGTV Episode
- A retell of Washington Irving's 1820 Halloween novel.
- What happens when Continuum's future cop and pulled-from-the-past Sleepy Hollow's Ichabod Crane team up? You get some temporal shenanigans.
- The Halloween classic rides again. Doug gives his thoughts on why this short has stayed with people for so many years. Let's take a look at "Sleepy Hollow" on a new episode of Dark Toons.
- The name "Sleepy Hollow" is engraved in popular culture and is synonymous with one of the most famous ghost stories in the world, that of the Headless Horseman. The "Most Haunted" team heads down to the cemetery and sets up camp at the location of the infamous wooden bridge; it is said that one can hear the hooves of the famous horseman galloping across it in the dead of night.
- 2008–TV Episode
- Looks like our heroes have found themselves stuck in one eerie neighborhood. Only escaping the street of Sleepy Hollow Way can break the curse. Beware the Headless Horseman.
- 2015– 16mTV Episode