Scary Pumpkin Headless Horseman Halloween Tees Co
Scary Pumpkin Headless Horseman Halloween Starry Night T-Shirt, Men, Black, 3X-Large
$16.99on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
Disney Animation
The Headless Horseman
The Headless Horseman is the ghost of a soldier who rides through Sleepy Hollow at night, looking for the head he lost to a cannonball. Washington Irving introduced him in The Legend of Sleepy Hollow, published in 1820 in The Sketch Book, where the local legend says he was a Hessian trooper killed in the Revolutionary War.
- First appearance
- The Legend of Sleepy Hollow (1820), Washington Irving
- Created by
- Washington Irving
- Also known as
- Headless Horseman of Sleepy Hollow
- Universe
- The Legend of Sleepy Hollow
- Appears in
- books, animation, film, television
Who is The Headless Horseman?
The Headless Horseman is the ghost of a soldier who rides through Sleepy Hollow at night, looking for the head he lost to a cannonball. Washington Irving introduced him in The Legend of Sleepy Hollow, published in 1820 in The Sketch Book, where the local legend says he was a Hessian trooper killed in the Revolutionary War. The story's schoolmaster, Ichabod Crane, is chased by the Horseman, who throws what appears to be his head — a pumpkin — and Ichabod is never seen in the village again. Irving leaves it open whether the ghost was real or a rival in disguise. Disney's 1949 animated version, part of The Adventures of Ichabod and Mr. Toad and narrated by Bing Crosby, made the chase one of the most famous sequences in American animation and a Halloween television staple. Tim Burton's Sleepy Hollow in 1999 gave the Horseman a head, and a face, played by Christopher Walken. The real village of North Tarrytown, New York, renamed itself Sleepy Hollow in 1996. The flaming jack-o'-lantern and rearing black horse are the usual designs.
The Headless Horseman: the details
- First appearance
- The Legend of Sleepy Hollow, Washington Irving, 1820
- Published in
- The Sketch Book of Geoffrey Crayon, Gent.
- The legend
- A Hessian trooper who lost his head to a cannonball
- His victim
- The schoolmaster Ichabod Crane
- Disney version
- The Adventures of Ichabod and Mr. Toad, 1949, narrated by Bing Crosby
- Film
- Sleepy Hollow, 1999, with Christopher Walken
- A real town
- North Tarrytown, New York, renamed itself Sleepy Hollow in 1996
Why The Headless Horseman endures
America's best-known ghost story character, and a fixture of Halloween since 1820.
What The Headless Horseman looks like on a shirt
Signature motif: Headless rider on a rearing black horse, holding a flaming jack-o'-lantern
A silhouette against a full moon is the classic design. Orange and black suit Halloween ranges.
Moonlit silhouettes and jack-o'-lanterns; strong October seller for adults and older children.
The Headless Horseman T-shirts
See all on Amazon →
Funny Family Matching Couple Halloween Costume
Headless Horseman Scary Pumpkin Spooky Classic Halloween T-Shirt
$14.99on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
Scary Horseman Pumpkin Halloween Mens Boys Tat
Headless Horseman Scary Pumpkin Halloween Mens Boys T-Shirt, Men, Black, 3X-Large
$13.79on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
Scary Pumpkin Headless Horseman Halloween Custome
Gothic Sleepy Headless Horseman Spooky Pumpkin Halloween T-Shirt
$14.44on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
Midnight Horseman Gothic Halloween
Vintage Headless Horseman Pumpkin Rider Haunted Halloween T-Shirt
$13.38on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
The Legend Of Sleepy Hollow Headless Horseman
The Legend of Sleepy Hollow Headless Horseman Halloween T-Shirt
$13.98on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
Disney
Disney 100 The Headless Horseman of Sleepy Hollow Halloween T-Shirt
$19.99on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
Sleepy Hollow Pumpkin Headless Horseman Halloween
Sleepy Hollow Spooky Pumpkin Headless Horseman Halloween T-Shirt
$14.99on amazon.com · Sep 17, 2026
Check sizes and price on Amazon
Buying from outside the United States? Prices shown are amazon.com in US dollars. Links redirect international readers to their local Amazon, where pricing, sizing and availability are shown in local terms.
Price and availability are taken from Amazon at the time shown and can change. The price on Amazon at the time of purchase applies.
Sizes: kids to adult
These links run a live Amazon search for The Headless Horseman shirts in each US size band. Amazon shows what is currently listed; availability in a particular size is confirmed on the product page, not here.
| Band | Ages | US sizes | Search |
|---|---|---|---|
| Toddler | 2–4 years | 2T, 3T, 4T | Search toddler sizes |
| Kids | 4–7 years | XS (4/5), S (6/7) | Search kids sizes |
| Youth | 8–14 years | M (8), L (10/12), XL (14/16) | Search youth sizes |
| Adult | 15+ | S–3XL | Search adult sizes |
US sizing shown. Cut and measurement vary between brands — see the size guide before ordering, especially for youth sizes. Base search: Headless Horseman t-shirt.
Who has played The Headless Horseman
| Performer | Production | Year | Type |
|---|---|---|---|
| Christopher Walken | Sleepy Hollow | 1999 | Live action |
More from Disney Animation
All Disney Animation →More cartoons & animation
All cartoons & animation →The Headless Horseman T-shirts: common questions
Who created The Headless Horseman?
The Headless Horseman was created by Washington Irving, first appearing in The Legend of Sleepy Hollow in 1820 (Washington Irving).
What does a The Headless Horseman T-shirt usually look like?
Headless rider on a rearing black horse, holding a flaming jack-o'-lantern. Moonlit silhouettes and jack-o'-lanterns; strong October seller for adults and older children.
Are The Headless Horseman T-shirts made for children?
Yes — The Headless Horseman appears on our kids pages, and shirts are commonly made from US toddler 2T up through youth XL.
Who has played The Headless Horseman?
The Headless Horseman has been played on screen by Christopher Walken (Sleepy Hollow, 1999).
How much does a The Headless Horseman T-shirt cost?
The Headless Horseman shirts we currently track start from around $13.38 on amazon.com. Every price on this page is dated, because they move.
This profile was compiled from published reference material about The Headless Horseman — first appearance, creator credits and production history — and is a secondary source rather than a substitute for the original publication. Where a detail could not be corroborated it has been left out. We do not physically test garments; see how we work for what that means and what it does not.
Reference. This profile was compiled from published sources. For the character's full publication history see Wikipedia (Wikidata Q1475916). Our method and limitations are stated in full.
CharacterTshirts.com is an independent guide. It is not affiliated with, authorized by, endorsed by, or connected to any character rights holder, publisher, studio or network named on this site. All character names and titles are trademarks of their respective owners and are used here only to identify the products described.