Carving pumpkins into a jack-o-lanterns is a longstanding family tradition in many American households. I always marvel at my neighbors’ expertly carved masterpieces while my attempts to make a macabre gourd most closely resemble “American Horror Story’s Beauregard”. Thus, I find it far more fun and incredibly more rewarding to make jack-o-lanterns digitally. At least Photoshop lets me hit the “undo” button!

1. Creepers by Derek Holiday

I love the wicked glowing grin in this promotional design for a Canadian Halloween store.

Creepers by Derek Holiday

2. Jack-o-Lantern by Matheus Horstmann

This creepy pumpkin head is whimsical yet disturbing, especially with the noxious green vapors trailing from its grin.

 Jack-o-Lantern by Matheus Horstmann

3. Pumpkin Head by Kristina Mansson

A clever design featuring a skull made out of jack-o-lantern silhouettes.

 

4. Carving Contest by Lisa Shipley

A poster or flyer design for a pumpkin carving contest, I like this design for its unique font and the happy/sad jack-o-lantern combination.

Carving Contest by Lisa Shipley

5. Halloween Flyer by Dushan Stojkovich

This is a template design that’s actually worth using for a Halloween party poster or flyer.  I like the disco ball jack-o-lantern featured in the center.

Halloween Flyer by Dushan Stojkovich

6. Krunkin Pumpkin Ale by Scott Schwieterman

Krunken Pumpkin Ale’s label design makes it look like the kind of brew you’d want to swig at a bachelor party.

Krunkin Pumpkin Ale by Scott Schwieterman

7. Pumpkin’s Prom by Katerina Frolova

A wicked pumpkin patch gets treated with eerie details, made even creepier by the artwork’s title.

Pumpkin’s Prom by Katerina Frolova

8. Greedy Halloween Pumpkins by Tina Marie Lane

The O’lantern family after trick or treat, but the mad glowing grins still makes them creepy characters.

Greedy Halloween Pumpkins by Tina Marie Lane

9. Pumpkin Party by Debi Pickler

I’m not sure if this design is creative, surreal or realistic. Either way, I’ve never seen toucans in a pumpkin patch. Maybe they’re hybrid pumpkins that grow in tropical climates?

Pumpkin Party by Debi Pickler

10. Pumpkins by Tavo Montanez

Next time you’re in a cornfield and you see this, turn and run. I doubt it would do any good, but at least you won’t see it coming.

Pumpkins by Tavo Montanez

11. Pumpkin Skateboard by Dan Brandon

Every skateboarding Halloweenophile should have one!

Pumpkin Skateboard by Dan Brandon

12. Pumpkin by Max Vasiliev

Light and shadow are interesting design elements in this design.  A foreground candle illuminates the jack-o-lantern, which shades the witch hat and is backdropped by a glowing moon.

. Pumpkin by Max Vasiliev

13. Spooktacular by Vincent Panzeca

Another horrifying cornfield dweller design, I like how it mixes elements of grunge and cut-out styles.

Spooktacular by Vincent Panzeca

14. Jack-o-Lantern by Genzoman

Attention to detail, excellent use of light and shadow, and a grinning mouth full of razor-sharp – and real – teeth make this design perfectly nightmare-worthy.

Jack-o-Lantern by Genzoman

15. Jack-o-Lantern by SeaGerdy

This cartoon jack-o-lantern would make a perfect Scooby Doo villain.  Or maybe Ben 10… ULTIMATE JACK-O-LANTERN!

Jack-o-Lantern by SeaGerdy

16. Jack In, Jack On, Jack Out by SavageSinister

Another nightmarish jack-o-lantern design that features a hand-illustrated or painted style.

Jack In, Jack On, Jack Out by SavageSinister

17. Halloween Tree by Jeremiah Morelli

The perfect scenery to start an unsettling Halloween night, complete with a “pumpkin tree” and owl. Surreal and cool: One can only wonder what fate befell the owners of the toys.

Halloween Tree by Jeremiah Morelli

 

18. Obsessed by Fegan

A bat-winged, stick-fingered man runs by with a flaming jack-o-lantern on his head. Kind of reminds me of college.

Obsessed by Fegan

19. Trick o’ Lantern by Christopher Crow

This is what happens when you leave the pumpkin too long on the vine.

Trick o’ Lantern by Christopher Crow

20. Jack by Eddie the Yeti

A skull-pumpkin morph makes the perfect jack-o-lantern design!

Jack by Eddie the Yeti

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20 Wicked Jack-O-Lantern Design Inspiration