Look. We’ve all been there. You get that "All-Hands" email in early October with a subject line full of ghost emojis, and you just know you’re about to spend forty dollars of your own money on a gourd that will rot on your desk by Tuesday. It's the office pumpkin decorating contest. Usually, it’s a bit of a drag, right? But it doesn't have to be a chore if you actually lean into work pumpkin contest ideas that move past the tired "scary face" trope.
Most offices fail at this because they try too hard to be "corporate fun." You know what I mean. The HR-approved fun that feels like a mandatory homework assignment. To actually get people excited, you need to ditch the perfectionism. I’ve seen teams get more competitive over a pumpkin carved to look like the company’s slowest-loading software interface than they ever did over a classic Jack-o'-lantern.
Why Most Work Pumpkin Contests Fall Flat
The biggest mistake? Lack of a theme or, conversely, a theme that is way too restrictive. If you tell everyone to "be creative," they panic and do nothing. If you tell them it has to be "spooky," you get twenty identical orange blobs with triangle eyes.
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I talked to a few office managers who swear by the "Pun-Kin" approach. Basically, you only allow pumpkins that represent puns. Think "Pumpkin Spice" (a pumpkin wearing a tuxedo and holding a ginger jar) or "Gourd-geous" (a pumpkin with way too much highlighter and fake lashes). It gives people a prompt. People love prompts. Without them, you're just staring at a vegetable wondering why you didn't just stay home and watch Netflix.
Honestly, the mess is another factor. Nobody wants to scoop out pumpkin guts in the breakroom next to Mike’s ham sandwich. If you’re planning this, you've gotta decide early: are we carving or are we painting? Painting is cleaner, but carving allows for that gross, visceral October vibe we all secretly crave.
The Best Work Pumpkin Contest Ideas for Competitive Teams
If your office is the type where people track their KPIs like they're training for the Olympics, you need high-stakes categories. Don't just do "Best Overall." That's lazy.
The "Corporate Horror" Category
This is where the real magic happens. Instead of ghosts, have people decorate pumpkins to represent work-related nightmares. A pumpkin with a "Low Battery" icon painted on it. A pumpkin covered in sticky notes that all say "URGENT." Maybe a pumpkin that looks exactly like a Zoom call where everyone's camera is off. It’s cathartic. It lets the team blow off steam about the actual stresses of the job while still being "festive."
The Diorama Approach
Forget the single pumpkin. Tell teams they have to create a scene. I remember one tech firm in Austin where a team used three small pumpkins to recreate the "distracted boyfriend" meme. It was brilliant. They used felt, some old doll clothes, and a lot of hot glue. It won by a landslide because it was culturally relevant. If you want your work pumpkin contest ideas to actually land, they need to be shareable. They need to be something people want to put on their Slack channel or LinkedIn.
Use Non-Pumpkin Materials
Who says it has to be a pumpkin? Okay, it's a "pumpkin" contest, but some of the best entries use the gourd as a base for something else entirely. Turn it into a disco ball with silver sequins. Hollow it out and make it a functional cooler for sodas. Or, my personal favorite, the "Trash-o-lantern" where you only use recycled office supplies—paperclips for hair, rubber bands for features, and old spreadsheets for a cape.
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Logistics: Don't Ruin the Breakroom
You have to be smart about the "where" and "when." If you make people do this on their lunch break, they'll hate you. Period.
Schedule an hour on a Friday afternoon. Provide the pumpkins. If you ask employees to bring their own, half of them will forget, and the other half will buy the saddest, tiniest gourds available at the CVS down the street. Buy the big ones from a local patch or a grocery store bulk order. It costs the company maybe a hundred bucks, but the goodwill it buys is worth way more.
Pro tip: Buy those plastic tablecloths from the dollar store. Cover every single surface. Pumpkin juice is surprisingly sticky and smells weirdly like melon after three hours.
The Judging Process Needs to Be Fair (Or Hilariously Biased)
Don't let the boss pick the winner. It feels like favoritism, even if it isn't. Use a "People’s Choice" system. Give everyone three stickers. They walk around the "gallery" and slap a sticker on the ones they like. Most stickers wins.
Or, go the opposite way. Create absurdly specific awards:
- "The Pumpkin Most Likely to Start a Fire (Visually)"
- "The Pumpkin That Looks Most Like Our CEO"
- "The Most Minimalist (Lazy) Effort"
- "The Most Disturbingly Realistic Texture"
Specific prizes are better than one big prize. A $10 gift card to the coffee shop downstairs for "Best Use of Glitter" is more fun than a single $50 prize for one person. It spreads the joy around.
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Dealing With the "I'm Not Creative" Crowd
Every office has them. The accountants, the data analysts, the people who think "creativity" is a four-letter word. You've got to give them an out.
Suggest "Tech-o-lanterns." They don't have to be artsy. They can be precise. Give them some old circuit boards and some LEDs. A pumpkin with a functioning motherboard inside is way cooler than a poorly painted cat. Or suggest the "No-Carve" options. Stickers, Sharpies, and spray paint. It lowers the barrier to entry.
What Most People Get Wrong About Office Contests
The biggest failure is the "Aftermath."
Usually, the pumpkins sit on a ledge until they start to cave in on themselves and attract fruit flies. It's gross. Set a hard "Take It or Toss It" date. Typically, November 1st is the day. If it’s still there on the 2nd, it goes in the bin. No exceptions.
Also, avoid the "Sexy Pumpkin" or overly political stuff. It seems obvious, but someone always tries to push the envelope. Keep it HR-friendly without being boring. It’s a fine line, but usually, if you have to ask "is this okay?", the answer is probably no. Stick to pop culture, inside office jokes, or classic spooky themes.
Taking Action: Your 3-Step Plan
If you're the one in charge of this, don't overthink it.
- Pick a Theme Immediately: Don't leave it open-ended. Choose "Pop Culture Icons" or "Office Inside Jokes" or "The Pun-Kin Challenge."
- Set a Fixed Time: Do it during work hours. Provide the snacks. Cider and donuts go a long way in making people feel like they aren't just doing extra work.
- Define the Categories Early: Let people know what they're playing for. Is it for the "Scariest" or the "Funniest"? Knowing the "rules of engagement" helps the less-creative folks find a starting point.
Get the pumpkins on a Tuesday. Do the decorating on a Thursday. Judge on Friday. Toss them by Monday. That's the perfect lifecycle of a successful office event. It's short, impactful, and doesn't overstay its welcome.
Start by sending out a poll today to see which theme people prefer. Giving them a choice in the theme makes them "owners" of the event rather than just participants. You'll get way more buy-in that way. Then, hit up a local wholesaler for the gourds. You're looking for the ones with character—bumps, weird stems, and odd shapes usually make for the best "character" pumpkins anyway.