Headless Horseman Pins and Buttons

Original painting by artist Craig Mahoney

Headless Horseman

Headless Horseman....You can't reason with a headless man!

Headless Horseman

Bring home the legend of Sleepy Hollow!

The headless Hessian rides again tonight! No mini fig is safe on Hallow's Eve!

The Headless Hessian's nightly ride. Copyright © 2022 by J.E.Larson

The classic Headless Horseman in the grave of his victims

Sleepy Hollow

A quick design.

Beware his pumpkin stare! Do you hear the horse that brays in the pale moonlight?

Headless Horseman

Headless Horseman

Headless Horseman

Beware the rider with no head, he may take yours as his own!

Headless Horseman

I had an old flaming pumpkin design, so why not do a little headless horseman?

This illustration features the famous Headless Horseman.

The ride of the Headless Horseman at Mickey's Not So Scary Halloween Party is one of my favorite parts of the special event! It's amazing to see him ride by on his dark horse with his glowing jack-o-latern head. Cinderella Castle looks beautiful lit up in Halloween colors. Bring some spooky magic into your home with this design showcasing the Headless Horseman at the Magic Kingdom!

Take it to the paint!

A quick design.

Headless Horseman of Legend on a Rearing Black Horse

Headless Horseman

A quick design.

The Legend of Sleepy Hollow, The Headless Horseman

Get your hands on this Drewbacca exclusive design. Wear a conversation piece among envious eyes or give the best gift someone will ever receive! (Ok, maybe not the best, they might have been given a lightsaber or a puppy at some point, but it'll still be pretty cool!)

It's the headless horseman!

The Headless Horseman ready to ride this Halloween.

A spooky Halloween design of The Headless Horseman of Sleepy Hollow.

Sleepy Hollow

From downtown, Sleepy Hollow

Explore the mystery of folklore with our 'Headless Horseman - Sleepy Hollow' design. Inspired by a well-known fashion emblem, this design presents an intriguing reinterpretation: the headless horseman takes the place of the traditional polo jockey. The headless silhouette emerges in a subtle play of style and horror, capturing the essence of Sleepy Hollow's legendary story. With elegance and a haunting touch, this design fuses classic fashion with the dark narrative of folklore.

The Headless Horseman ready to ride this Halloween.

You can't reason with a headless man!

Headless Horseman

Headless horseman