Headless Horseman Long Sleeve T-Shirts

A terrifying apparition emerges from behind a huge twisted tree. It's a dark rider on a darker horse. He carries a flaming jack-o-lantern raised and ready to hurl at you. Most terrifying of all, he lacks his head. Meet the Headless Horseman of Sleepy Hollow. This is an image I've wanted to create for a while. So, for Halloween 2022, I felt time was ripe. The Headless Horseman is a ghost of folklore that can be found in many parts of Europe and America. Usually, the specter is carrying his head in the saddle, but the most famous version is that of Sleep Hollow, made popular by the short story "The Legend of Sleepy Hollow" by Washington Irving. This version of the Headless Horseman carries a jack-o-lantern (or maybe a pumpkin)....

Headless Horseman

Illustration of the headless Horseman. "The Legend of Sleepy Hollow" is a gothic story by American author Washington Irving, first published in 1820 where a headless horseman soldier decapitated by a cannonball in battle is roaming the land in search of his missing head.

Halloween Night Headless Horseman

With a hip-hip and a clippety clop, he's out looking for a top to chop. So don't stop to figure out a plan, you can't reason with a headless maaaaan.

A spectral rider on a demon horse heralds the holiday of Halloween. Saddle up and join the ride!

My version of the Headless Horseman from The Legend of Sleepy Hollow

illustration of a bucking horse with his headless rider

The Hessian selects just the right pumpkin to present to his schoolteacher friend. Copyright © 2023 by J.E.Larson

The Hessian who was also Headless

The headless horseman rides!

Headless Horseman

Grim Reaper

Headless Horseman

The Headless Horseman ready to ride this Halloween.

A Sleepy Hollow inspired beer label featuring the Headless Horseman

Headless Horseman

A cute little horseman!

The Headless Horseman ready to ride this Halloween.

A spooky design I made for Halloween of The Headless Horseman of Sleepy Hollow

Headless Horsemen design

Beware the Headless Horseman Corgi is out for a run on this Halloween night!

Headless Unicornman

This fun illustration features the headless horseman, perfect for Halloween.

Fan of the sleepy hollow legend then you'll like this Pub and Inn design as the headless horseman is drinking a beer on halloween eve. Drink up freaks!

Headless Horseman

Headless Horseman

The ultimate Halloween costume.

Necklaces available in my Etsy shop @Luguardio

With a hip-hip and a clippity-clop He's out lookin' for a top to chop So don't stop to figure out a plan You can't reason with a headless man

Headless Horseman taking a break for his pumpkin spice ice coffee. Everybody deserves some time off

Cool Cars for Cool Customers Private Hearse Club Est. 1962

"With a hip, hip and a clippity clop He's out looking for a head to chop So don't stop to figure out a plan Cause you can't reason with a headless man"

A ghostly horseman on a demon steed charges through Halloween night, inviting you to join him. Ride with him or get a flaming pumpkin in the face. Your choice.