Headless Horseman Hoodies

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

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.

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

Halloween Night Headless Horseman

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

illustration of a bucking horse with his headless rider

The Hessian who was also Headless

Headless Horseman

The Headless Horseman ready to ride this Halloween.

A Sleepy Hollow inspired beer label featuring the Headless Horseman

Grim Reaper

Headless Horseman

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

Headless Horseman

A cute little horseman!

The headless horseman rides!

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

The Headless Horseman ready to ride this Halloween.

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

Headless Unicornman

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!

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

Headless Horseman

Headless Horseman

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

Necklaces available in my Etsy shop @Luguardio

"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"

Headless Horsemen design

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

Headless horseman on a black steed with a Jack O Lantern on his head and whip in his hand, set against a dark nightscape. Text: On the Hunt.

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.

Headless Horseman - The Ichabod Crane Equestrian School, Sleepy Hollow New York. We have been training Headless Hessians since 1790! Wear the authentic Ichabod Crane Sleepy Hollow Gear. This is a great tourist design for anyone visiting Ghostly Haunts. Hand Drawn graphics in a classic branded badge design shows Jack-o-Lantern and Jumping Horses with Old Timey Text.

The ultimate Halloween costume.