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Suptober - A Supernatural Creative Challenge

@suptober.bsky.social

Welcome to Suptober! A daily art challenge throughout the month of October with creations themed around the show Supernatural! Originally a challenge by @winchester-reload. Use #suptober25 for us to see your work!

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Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 31 | Halloween! 🎃 — #suptober25 #spnfanart #destiel

A digital illustration of three pumpkins, two of them off to the sides with a bigger one in the middle. Carved into the bigger pumpkin reads “Happy Halloween!” Sitting on the pumpkin is Castiel dressed in a red sparkly jumpsuit with a deeeep v neck and short sleeves. It’s sparkling red and he’s wearing purple shoes and has high purple gloves. He is supposed to look like a male version of Jessica Rabbit. He’s gentle holding Dean’s face close to him to give him a smooch on the cheek. Dean is dressed as Roger Rabbit and is laughing.

Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 30 | Decor — #suptober25 #destiel #spnfanart #spnfandom

A digital illustration showing the front of a house with a porch and theee steps leading down to a stone path. On the path is. Box labeled Halloween decor. Next to the box on the lawn are pumpkins and corn stalks. There are two pots of mums next to the stairs. Up the stairs, Dean and Cas share a smooch as Dean is about to string up some orange lights on the gutter and Cas is tying another bunch of corn stalks around one of the pillars Holding up the roof over the porch. A few leaves are flying by in the wind.

Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 29 | Closet — #suptober25 #destiel #spnfanart #spnfandom

A digital illustration depicting Castiel sitting on on a bed, cross legged, looking up at Dean standing nearby. Cas is looking as a burgundy plaid shirt that Dean is holding up against himself, and Cas is thinking. Around them and on the bed are various shirts and ties. There’s text in the upper right saying “Getting ready for their anniversary date…”

Verónica Vanesa Pereyra @verobatto.bsky.social · 9mo ago

@suptober.bsky.social Day 30: Decorating He is, tho. #destiel #suptober25 #spnfamily

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Rauko @fearauko.bsky.social · 9mo ago

Had to draw #dodio pirate wives for #suptober25 Day 21: Ladies of #Spn #JodyMills #DonnaHanscum #SpnLadies #SpnArt

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Rauko @fearauko.bsky.social · 9mo ago

Dean thrust the shovel into the dirt. “It doesn’t end like this,” he told the covered form on the ground. “It can’t." Fic Link: archiveofourown.org/works/178740... ... Barely scraped together time to do anything for #Suptober25 Day 20's prompt: Haunted, but...(1/2)

pencil sketch of Dean on his hands and knees beside Cas's freshly-dug grave

Rauko @fearauko.bsky.social · 9mo ago

Did a young Dean and Usagi/Serena role swap for Day 17's #suptober25 prompt: Crossover. (Also using it for the "Transformation Sequence" square on my DeanCas Anime Bingo card.) Not pictured are Sam and Cas having a collection of crises. #DeanWinchester #TsukishiroUsagi #Spn #SpnArt #SailorMoon

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Rauko @fearauko.bsky.social · 9mo ago

Trauma doesn't just disappear. You don't cling that tightly to the lifeline of power unless you remember well what it was like to be powerless and scared. Had to draw #RowenaMacLeod my beloved for Day 15's #suptober25 prompt: Nightmare. #suptober #spnart

Rowena asleep, dreaming about when she gave birth to Crowley

Rauko @fearauko.bsky.social · 9mo ago

For day 14 ("Can you hear me?") of #suptober25 I had to draw Crowley from "A Howl at That Moon: What Goes Around Don't Come Around (or Maybe It Does)" because I know we talk about a Cas Empty rescue a lot, but sometimes I think about #Crowley ...(1/2)

Crowley from Supernatural sitting in the empty

Rauko @fearauko.bsky.social · 9mo ago

First #suptober25 prompt I actually found time to do this year. Have some #destiel in a hammock for Day 13: Stargazing #spnart #suptober Prompt List: bsky.app/profile/supt...

Dean Winchester and Castiel in a hammock, stargazing

Suptober - A Supernatural Creative Challenge@suptober.bsky.social · 10mo ago

It's October, meaning it's time for the Suptober creative challenge! Based on @winchester-reload original challenge for the Supernatural fandom <3 Remember to tag #suptober25 on here or tumblr if you make anything! #spnfamily #supernatural

A picture with two side by side lists with various decorations around including cornstalks, ghosts, a vampire, a bubbling cauldron with green bubbles, and pumpkins. The list is for every day of October and has a different word for each day, serving as a prompt for creating something for the TV show Supernatural. The list is:
Pumpkin, picnic, garden, orchard, lost, campfire, surprise, fortune telling, rainstorm, power outage, blanket fort, sunrise/sunset, stargazing, can you hear me?, nightmare, freckles, crossover, seance, flying, haunted, ladies of SPN, undercover, carnival, cemetery, game night, witchcraft, baking, fireworks, closet, decorating, and Halloween!

Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 28 | Fireworks — #suptober25 #spnfanart #spnfandom

A digital illustration depicting a grassy field at night with the Chevy impala from Supernatural in the foreground, parked. Out in the field, the night sky is lit up with some fireworks. Dean, Cas, Sam and Jack stand watching. Cas and Sam have sparklers in their hands.

Verónica Vanesa Pereyra @verobatto.bsky.social · 9mo ago

@suptober.bsky.social Day 29: Closet He's out. #spnfamily #destiel

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Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 27 | Baking — #suptober25 #destiel #spnfanart #spnfandom

A digital illustration depicting a table adorned with trays of autumn deserts. A pumpkin pie sits on a little pedestal cooling in the air. Next to it on a circle plate are 9 cupcakes with a swirl of white frosting and brown sprinkles that make it look like a cartoon ghost. Just in frame off in the bottom right corner are cookies with a Reese’s mini cup in the middle with little frosting for eyes and lines of chocolate for legs to mimicking a spider. Castiel is sitting on a chair holding a piping bag that has organelles frosting in it as he pipes it onto a tray of cookies before him to make pumpkins. There’s a small bowl of sprinkles next to him to make the pumpkins into Jack o lanterns. There’s a trivet on the table waiting for a hot tray. Next to it is a used piping bag that has white frosting in it. Dean is in the background walking toward the table with a tray of fresh cookies, saying “last batch!”

Verónica Vanesa Pereyra @verobatto.bsky.social · 9mo ago

@suptober.bsky.social Day 28: Fireworks #destiel #spnfamily Smooch

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Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 25 | Game Night — #suptober25 #spnfandom #spnfanart #supernatural

An illustration depicting Sam and Dean Winchester, Castiel, and Jack from Supernatural. The illustration looks like part of the original cover art for the game Twister. However in the original illustration everyone is laughing. This one is more realistic as Jack with the spin board is laughing. Cas is also laughing off to the right as he sits watching. Sam is panicking as he’s going to have to some how move his left foot to a red circle which is nearly impossible to do. Dean is on all fours looking up at Sam grumpy. Sam is saying “The hell you mean it’s red?” Referring to the spin board. Dean is saying “you better not kick me in the head again”.

Verónica Vanesa Pereyra @verobatto.bsky.social · 9mo ago

@suptober.bsky.social Day 27: baking. I can relate. #suptober25 #castiel #destiel #spnfamily

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Witchy-Worm @witchy-worm.bsky.social · 10mo ago

Suptober day 14 - Can You Hear Me #spn #destiel #suptober25

Digital Art. Giant Castiel standing in front of Dean. Castiel has 6 sets of wings, a glowing golden halo, and blue glowing eyes.

Wigglebox @wigglebox.bsky.social · 10mo ago

Suptober - Day 21 | Ladies of SPN (The Winchesters) — #suptober25 #thewinchesters #supernatural #spnfanart #spnfandom

A picture featuring Millie, Latika, Mary, and Ada from The Winchesters. They are sitting around a table that is laid out with a big bowl of glowing green liquid that has lightning like plants shooting out of it. Latika is holding a smaller bowl with a smaller lightning like plant coming out of it. There are three candles, a notepad, a jar of incense sticks, and a platter of what looks like long leaves also on the table. Latika is looking at the bowl happy that something is coming out of it. Mary is next to her on Latika’s right (center of the image for us) looking at the bowls in amazement. Ada is on the far left of the illustration looking up at Millie Winchester who is standing behind Lata and Mary. Millie is looking fondly back at Ada. Ada has a hand that’s funneling something that looks like glowing sand into the bigger bowl. The green casts a green glow on their faces and shadows behind them.

Deanna Marie SPN NJ 26 @dee4dean.bsky.social · 10mo ago

Suptober 2025 Day 21: Ladies of SPN Donna is my favorite, so here ya go. #suptober25 #spnfamily #digitalart #donnahanscum

A digital drawing of Donna Hanscum from Supernatural. She is wearing a police officer uniform and eating a powdered donut.

Wigglebox @wigglebox.bsky.social · 10mo ago

Suptober - Day 22 | Under[the]cover — #suptober25 #destiel #spnfanart #spnfamily

An illustration depicting a bedroom at night. The color tone is dark browns and oranges. There are two windows in the back wall, one with the blinds drawn and another with the blinds half up. On the left window where the blinds are half up there is a pumpkin window lamp stuck to the glass by a suction cup. It’s the only source of light in the room. In the center of the photo there is a bed with two figures under a blanket, engaged in… elicit affairs. This is Dena and Cas from Supernatural. They are silhouetted by the lamp behind them and off to the left. The blanket is illuminated. Their bed is in disarray with another blanket haphazardly laying half on the bed and half on the ground. There is also a pillow on the ground. In the foreground is an end table with a lamp that’s off and a phone and a glass of water.

Deanna Marie SPN NJ 26 @dee4dean.bsky.social · 10mo ago

Suptober 2025 Day 22: Undercover “Come on, Cas, really?” - Dean Cas tries so hard to blend in. #suptober25 #undercover #destiel #spnfamily

Digital painting of Castiel and Dean Winchester from Supernatural. They are both dressed in suits and ties, Castiel is wearing his trench coat over his suit and holding a fake FBI badge upside down. Dean is looking at him and thinking “come on, Cas, really?”

Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 23 | Carnival — #suptober25 #spnfanart #spnfamily

An illustration depicting a giant house with a scary vintage looking clown face and its open mouth as the entrance. The windows are glowing and the house is green and everything looks a little wonky. It’s a funhouse but it’s a scary one and so the sign says “fear house”. There is a line of people waiting to go in. In the foreground is Sam Winchester, Dean Winchester, and Castiel. Dean has a smirk on his face as he points to the house saying “c’mon Sammy, don’t be a coward.” Sam has his back to us with his shoulders tight exclaiming “I’m not a coward!” Cas has his head turned looking up at the house.

Wigglebox @wigglebox.bsky.social · 9mo ago

Suptober - Day 24 | Cemetery — #suptober25 #spnfanart #spnfandom #supernatural

An illustration depicting a foggy cemetery. Castiel is looking up at an angel statue atop of a grave. The angel is crying in grief. He’s looking up at it curiously. Her wings are extended and so are his. There are random tombstones in the foreground and background. Behind Cas is Dean Winchester who is holding a shovel and looking at Cas. Below Dean is Sam in a freshly dug grave. Sam is looking annoyed at Dean not paying attention.

Verónica Vanesa Pereyra @verobatto.bsky.social · 10mo ago

@suptober.bsky.social Day 22: Undercover Season 6 ruined us... #suptober25 #destiel #spnfamily

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Verónica Vanesa Pereyra @verobatto.bsky.social · 10mo ago

@suptober.bsky.social Day 23: Carnival #suptober25 #spnfamily

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Verónica Vanesa Pereyra @verobatto.bsky.social · 10mo ago

@suptober.bsky.social Day 24: Cemetery. He's cute. #Castiel #spnfamily

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Verónica Vanesa Pereyra @verobatto.bsky.social · 9mo ago

@suptober.bsky.social Day 25: Game Night #destiel #spnfamily

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Verónica Vanesa Pereyra @verobatto.bsky.social · 9mo ago

@suptober.bsky.social Day 26: Witchcraft. The queen. #spnfamily

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Verónica Vanesa Pereyra @verobatto.bsky.social · 10mo ago

@suptober.bsky.social Day 21: ladies of SPN #SONfamily #suptober25

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Verónica Vanesa Pereyra @verobatto.bsky.social · 10mo ago

@suptober.bsky.social Day 20: Haunted #suptober25 #spnfamily

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