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Collection of Sleepy Hollow Cliparts (72)

Looking for Sleepy Hollow Cliparts? Here you will find a carefully collected gallery of free images in high quality. Each Sleepy Hollow Cliparts can be downloaded for school projects, presentations, websites or creative designs. Need a custom image? Try our free image generator. These cliparts are free for personal use. Please read the full terms of use.

Distinctive sleepy hollow artwork spanning outline drawings and flat vector icons, prepared for fast reuse without background cleanup.

Silhouetted rider on rearing horse holding a carved jack-o'-lantern against a stormy sky.
A haunting Halloween rider on a wild horse, brandishing a carved pumpkin under a storm-lit sky.
Black-and-white illustration of a historic stone chapel with Gothic windows, small steeple, and surrounding graveyard with tombstones and trees.
A finely detailed 19th-century woodcut showing a modest stone chapel nestled among trees, complete with arched windows, a spire-topped bell tower, and an old graveyard.
A dramatic 19th-century engraving of two riders racing across a broken bridge at night, one brandishing a sword, with a church in the background.
Two riders gallop across a splintered wooden bridge under moonlight-one wielding a sword, the other clutching a glowing pumpkin-evoking Irving’s timeless tale.
A vintage woodcut illustration of a small stone chapel with a bell tower, surrounded by trees and a picket fence with gravestones.
A finely detailed 19th-century woodcut depicting a quiet rural chapel with arched doorway, bell tower, and surrounding graveyard.
A ghostly rider with a jack-o'-lantern head gallops on a skeletal horse against a black background.
The legendary Headless Horseman rides at midnight-his glowing pumpkin head held high as his horse leaps through the dark.
Paper cutout of Headless Horseman on black horse, holding jack-o'-lantern and whip, Halloween-themed craft.
A hand-colored paper puppet of the Headless Horseman riding a rearing black steed, holding a glowing jack-o'-lantern and whip-ideal for storytelling or decoration.
Black-and-white stylized bare tree with swirling branches and roots, forming a decorative corner frame on white background.
A minimalist yet expressive hand-drawn tree, perfect for framing text or adding organic elegance to digital designs.
sleepy hollow logo
The image is a rectangular frame with a white background. Inside the frame, there is a black text written in a cursive font that reads "Sleepy Hollow". The text is written in all caps and is in a dark, hand-drawn style. The frame is decorated with a floral pattern on either side. The overall design is simple and elegant.
A headless horseman on a rearing horse, holding a glowing jack-o'-lantern, chases a terrified boy under a full moon in a spooky forest.
A classic depiction of the Headless Horseman from Washington Irving’s *The Legend of Sleepy Hollow*, capturing suspense and autumnal dread.
A cartoon man in purple rides a startled white horse at night, as the Headless Horseman chases them through a spooky forest under a full moon.
Ichabod Crane clings to his nervous horse as the legendary Headless Horseman gives chase-classic spooky storytelling brought to life.
Historic wooden mill beside a waterfall, shaded by weeping willows and surrounded by stone foundations and rustic structures.
A classic woodcut illustration of a rural watermill, complete with cascading falls, timber framing, and lush weeping willows framing the scene.
A knight on a rearing dark horse brandishes a sword and flaming torch above a tombstone, draped in a flowing cape.
A legendary knight charges forward, sword raised and torch ablaze, as his steed rears above an ancient gravestone.
A startled man with a long nose rides a dark horse through a moonlit forest path, leaves swirling around them.
Ichabod Crane flees in terror down a leaf-strewn forest trail as the Headless Horseman pursues-classic Washington Irving imagery reimagined.
A spectral rider on a black horse holds a glowing jack-o'-lantern under a full moon, evoking the Headless Horseman legend.
The iconic Headless Horseman rides through misty night skies, wielding a carved pumpkin lantern-symbolizing fear, folklore, and autumn tradition.
Sleepy Hollow Tarrytown Chamber of Commerce logo featuring Headless Horseman silhouette with jack-o'-lantern on horseback.
Official logo of the Sleepy Hollow Tarrytown Chamber of Commerce, evoking the legendary Headless Horseman against a light blue backdrop.
A Halloween-themed rider with a glowing pumpkin head and bat wings rides a dark horse with a yellow saddle.
A mysterious pumpkin-headed rider with leathery bat wings soars atop a sleek black horse, evoking classic Halloween folklore.
Haunted tree silhouette with rider on horse against glowing moon, mounted on black base, eerie Halloween-themed decorative lamp.
A moody, handcrafted lamp where twisted branches frame a spectral rider beneath a luminous moon-ideal for setting a mysterious ambiance.
Skeletal knight on a rearing skeletal horse, wielding a flaming skull-topped staff in dynamic ink illustration.
A dramatic pen-and-ink depiction of a deathly rider charging forward, every bone rendered with meticulous detail and motion.
Line drawing of a classic Coca-Cola glass bottle with iconic logo and contour shape.
A minimalist line drawing capturing the timeless silhouette and script logo of the original Coca-Cola contour bottle.
Silhouette of a mounted knight wielding a sword, enclosed in an ornate decorative frame.
A dramatic knight-in-armor silhouette, captured mid-gallop with sword raised, framed by intricate baroque-style scrollwork.
Cinderella dances with the Grand Duke as the Prince reaches out, a scene from Disney’s *Cinderella* (1950).
In this charming scene, Cinderella shares a dance with the Grand Duke-just as the Prince rushes in, recognizing her true identity.
A stern teacher in green addresses three smiling students seated at a desk with an open book.
A memorable scene from classic animation showing a teacher delivering a lesson while students listen with delight and curiosity.
Orange crescent moon with a sleeping face and a dangling tassel, stylized as a whimsical night symbol.
A playful crescent moon dozes peacefully, its gentle expression and dangling tassel evoking calm nighttime magic.
A dark, gnarled tree frames a full moon behind a silhouetted rider on a rearing horse wielding an axe.
A lone warrior rides a wild horse through the night, backlit by a luminous full moon and shadowed by a grotesque, ancient tree.
A spooky illustration of the Headless Horseman from "The Legend of Sleepy Hollow" against a zigzag orange-and-black background.
A dramatic black-and-white depiction of the Headless Horseman galloping through Sleepy Hollow, framed by festive Halloween zigzags.
A rider in a purple cape holds a jack-o'-lantern while mounted on a rearing black horse under a full moon with bats.
A mysterious rider brandishes a glowing jack-o'-lantern while riding a dramatic black steed beneath a haunted full moon.
Watermelon-themed summer greeting with glittery text "SUMMER IS HERE" inside a striped circular frame and green ribbon bow, plus sliced wedges below.
A cheerful “Summer Is Here” design featuring watermelon stripes, glitter text, a festive green bow, and juicy slices-ideal for kicking off warm-weather fun.
A silhouetted warrior on horseback brandishes a double-headed axe beneath leafy branches in dramatic monochrome.
A lone rider charges forward, axe raised-captured in high-contrast monochrome under dappled tree light.
A knight in red cloak rides a black horse across a wooden bridge at night, sword raised, as a white horse flees; moonlit hills and chapel in background.
A lone knight in crimson gallops across a weathered bridge beneath a luminous moon, his sword aloft, as a white steed retreats into the shadowed path.
A terrified animated character rides a white horse as a glowing blue ghostly figure looms behind in a dark night scene.
The rider clings desperately to their horse as a spectral blue ghost emerges from the darkness, eyes glowing with eerie menace.
Belle from Disney’s Beauty and the Beast in a golden-yellow ballgown with floral border framing.
Belle stands gracefully in her signature yellow ballgown, framed by delicate rose vines-a timeless tribute to Disney’s beloved heroine.
Glowing jack-o'-lantern with menacing carved eyes, nose, and jagged teeth lit from within by warm orange light.
The eerie glow of a hand-carved jack-o'-lantern brings classic Halloween spirit to life in this dramatic close-up.
Wooden basket overflowing with red apples and a green pear, with a handle and loose apple nearby.
A charming hand-drawn basket brimming with juicy red apples and a single green pear, evoking autumn harvest and wholesome goodness.
Open black coffin with rich red velvet interior and silver hinges, displayed against white background.
A striking black coffin with deep red velvet lining, open to reveal its refined interior and polished metal hardware.
A cartoon woman sleeping peacefully on her side, wearing pink pajamas and hugging a light blue pillow.
A serene sleeper curled up in soft pajamas, embodying comfort and restful slumber.
A spooky Halloween scene with a rider on a black horse holding a glowing jack-o'-lantern, under a full moon with bats and tombstones.
A spectral rider gallops through a haunted graveyard, lantern ablaze, as crows circle and pumpkins glow in the eerie night.
Silhouette of a pirate in profile wearing a tricorn hat and long braided hair with a curl at the end.
Classic pirate profile silhouette with tricorn hat and signature braided tail-ideal for vintage nautical designs.
Black and white stylized animal paw print with four toes and a pad, outlined in bold ink.
A clean, bold paw print design ideal for branding or educational use-simple yet expressive.
Gravestone with skeleton emerging from cracked stone, "RIP" carved below, set on grassy ground.
A classic haunted tombstone design featuring a dramatic skeleton bursting out of the stone, ideal for seasonal decorations or eerie storytelling visuals.
Black-and-white line drawing of a Celtic cross with interlaced knotwork at the arms' intersections.
A classic outline of a Celtic cross, featuring the distinctive ring connecting the arms and intricate knot patterns at each intersection.
Mickey Mouse laughing joyfully with one hand over mouth and the other raised in excitement.
Mickey Mouse caught mid-laugh, radiating pure delight and playful energy in his signature red shorts and yellow shoes.
Cartoon boy with blond hair slouching at a school desk, looking bored or embarrassed.
A cartoon student slouches at his desk, blushing and avoiding eye contact-ideal for illustrating shyness, distraction, or classroom fatigue.
a black horse with a sword on its back
The image is a digital illustration of a black horse with a red cape on its back. The horse is galloping with its front legs stretched out and its head turned to the side. The mane and tail are flowing in the wind. He is holding a sword in his right hand and appears to be in the middle of a battle. The background is transparent, making the horse and the mane stand out. The overall color scheme of the image is black and red, giving it a striking contrast.
the legend of sleepy hollow
The image is a graphic design with a yellow circle in the center. Inside the circle, there is a black silhouette of a tree with bare branches. The tree appears to be in a state of disrepair, with no leaves or branches visible. The background is white, and the text "The legend of Sleepy Hollow" is written in a cursive font in black. The overall design is simple and minimalistic.
a man riding a horse with a pumpkin on his head
The image is a digital illustration of a black horse with a red cape draped over its back. The horse is standing on its hind legs and is holding a yellow pumpkin in its right hand. The pumpkin has a skull-like face with a pointed nose and a small mouth. The background is white. The overall style of the illustration is cartoon-like and the horse appears to be in a fighting stance.
a pixel art of a man riding a horse
The image is a pixel art illustration of a knight riding a black horse. The knight is wearing a red and gold armor with a helmet and a cape. The horse is galloping with its front legs stretched out and its tail feathers flying behind it. The background is transparent, making the knight and horse the focal point of the image. The image appears to be a pixelated version of a video game or video game.
a black horse with a pumpkin on its back riding a black horse
The image is a digital illustration of a black horse with a pumpkin on its back. The horse is galloping with its mane and tail flowing in the wind. The man is wearing a green cloak and a red hat with a pointed brim. He is holding a sword in his right hand and a shield in his left hand. The pumpkin is orange with a jack-o-lantern face carved into it. The background is transparent, making the horse and the pumpkin stand out. The overall mood of the image is dark and spooky.
Black-and-white silhouette of the Headless Horseman riding a galloping horse, holding a glowing jack-o'-lantern head aloft.
A classic silhouette of the Headless Horseman charging forward with his carved pumpkin lantern raised high.
Hooded figure in tattered cloak holding a glowing jack-o'-lantern with menacing grin.
A shadowy hooded character grips a carved pumpkin with jagged, glowing teeth-ideal for spooky storytelling or costume design.
A vintage woodcut illustration of a rustic wooden bridge over a stream, surrounded by dense trees and a small cottage on a hill.
A finely detailed 19th-century woodcut showing a tranquil woodland setting, complete with a rustic bridge, gentle stream, and a quaint cottage nestled among tall trees.
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