On Saturday, October 17, a friend and I carved five pumpkins into helmets, loaded them into my little camping cart, and wheeled them all over downtown Victoria for a night of photos. Fan Tan Alley, under the Chinatown gate, Bastion Square, the Parliament Buildings all lit up, even inside the Bard & Banker.
That night was also the soft launch of Living Vicariously, my project about the space between wanting to do a thing and actually doing it. So this is the post where I share what it actually took... the preparation, the setbacks, and the small decisions, bruise included, so you can run your own version of it.
Where the idea came from
I kept seeing people online doing pumpkin head photo shoots, and I was inspired. That's the whole origin story... it wasn't my idea, I just finally stopped watching other people do it and did it myself. Every time one crossed my feed I thought the same thing, that looks like the most fun you can have for the price of a pumpkin. If it's been crossing your feed too, or you're just hunting for a fun Halloween idea that isn't another costume party, the rest of this post is everything I learned doing it, including the parts I would do differently.
Step zero: convince a friend
None of this works solo, or at least it doesn't work nearly as well. So the first real step was talking a friend into spending a Saturday carving pumpkins and then wearing one in public, and I had help with the pitch. I used Muse, Meta's AI assistant, to turn my half-formed idea into an actual plan... the five faces, a route through downtown timed to the light, pub stops along the way, even ground rules for the night. Then I sent my friend the plan, instead of a rambling "trust me, it'll be fun" text.
A plan is so much easier to say yes to than a pitch. He could see the whole night laid out: what it would cost, how long it would take, where we'd end up. He said yes. If you're recruiting your own pumpkin crew, steal that move. Put a plan in front of them. Vague enthusiasm is easy to decline... a plan with pub stops in it is not.
What you need
- Six pumpkins for five heads. Buy the spare, because one will crack or be weirdly thick. Go big, the Cinderella style carving pumpkins, 12 to 14 inches across... size is the whole game when the pumpkin has to fit over a human head.
- Carving tools, plus a sturdy scoop or scraper for thinning the walls
- Balaclavas, or dollar store toques with the eye holes cut out, one per pumpkin wearer (more on these below, they matter more than you'd think)
- Black outfits, so the pumpkin is the whole show
- A tripod, and a phone or camera with a timer
- A wagon or camping cart for moving five pumpkin heads around, because you are not carrying them all by hand
- Optional but recommended, and I say this from experience: a little piece of foam to cushion the top of your head
Build the helmets
1. Cut the bottom, not the top. Cut the opening in the bottom of the pumpkin so the stem stays on top like a proper jack-o'-lantern. Make the hole a little wider than your head and test-fit as you go, ears are the pinch point. And here's a tip I'm happy to pass on from experience now... when you flip the pumpkin over to cut the bottom, protect the stem. I carved mine in my lap, with the stem rested between my legs so it never took any weight. Don't just set it stem-down on a hard counter, those stems snap off easily, and a stemless pumpkin helmet loses half its charm.
2. Scoop it out well, but go gentle near the stem. Scoop out as much of the inside as you possibly can, because these things are heavy. It's weight sitting on your head every time you wear one, and that weight adds up on your neck as the night goes on. But go easy at the inside top where the stem attaches, because aggressive scooping there is how a stem gets damaged. That trade-off leaves a little bump inside the top of the pumpkin, right where it sits on your head, and it is not comfortable. I had a bruise on the top of my head and a headache by the end of the night. If I did this again, I would tuck a small foam insert inside the top as a buffer. Learn from my bruise.
3. Carve the face big. You're not just decorating the pumpkin, you are seeing out of it, through the eyes and the mouth together, and you want those expressions to show up well on camera. So carve both bigger than instinct says, and keep the shapes bold and simple... fine detail disappears in photos anyway. Ours all had different expressions, which is what made the photos so fun. One classic spooky grin, one with a big round surprised O for a mouth, one mid-scream, one angry, one lopsided and goofy.
4. Cover your head. We did not use anything fancy under the pumpkins. We bought dollar store toques and cut holes for the eyes. I'm calling it a toque because I'm Canadian... if you're reading this from somewhere else, you might know it as a beanie. A balaclava works just as well if you have one, it's the ski mask style with the eye holes and a mouth hole sewn in. Either way, it gives you a layer between your head and the inside of the pumpkin, and it keeps the whole look clean. Our ritual at every stop was pumpkins at our feet first, then toques on, then pumpkin heads on. Partly for the photos, and partly because we were very mindful of not wandering around downtown with our faces covered looking like we were up to something nefarious. Heads at your feet, toque on in the open, pumpkin on for the photo... nobody gives a second thought to two people doing that. Two people walking the streets already masked up is a different story.
5. Carve the day of. We carved Saturday afternoon and shot Saturday night. By the time we were out there the pumpkins were dry and totally fine, no elaborate preservation routine required. Afternoon carve, evening shoot, done.
Plan your route, then let the night happen
The single best piece of advice I can give you is to plan your route before you go, so the night unfolds in a logical order instead of zig-zagging across town. We mapped ours around downtown Victoria: Fan Tan Alley, the Chinatown gate, Bastion Square, and the Parliament Buildings once they were all lit up, with the Bard & Banker as our second-to-last stop. Think about when your hero location looks its best (for us, the Parliament Buildings after dark, all lit up) and build the order of your stops around that.
Two things to know about how the night actually works. First, you do not walk around wearing the pumpkin. Nobody does, or nobody sensible does. The heads travel in the cart, and they go on for the photo, come off, and go back in the cart. And handle them gently on those trips in and out, because somewhere in the second half of our night we grabbed one a little too quickly and split its face, so we finished the night with four heads instead of five. It happens in a second, and it's exactly why the spare pumpkin on the supply list isn't optional. Second, plan for the photos themselves to take longer than you think, which brings me to the part nobody warns you about.
The photography is the hard part
We had no photographer. It was the two of us, a tripod, and a ten second timer, which means one of us setting the shot, hitting the timer, and sprinting back to get a pumpkin on and into position before the shutter went. It worked, the photos in this post are proof, but it was hard, and it was the slowest part of every single stop. If you can recruit one more human to come along and take the photos, do it. It would have been so much easier. If it's just two of you, the tripod and timer absolutely get it done, just budget extra time per stop and bring your patience.
Be prepared to be a public spectacle
I knew the pumpkins would turn a few heads. I did not expect how many people would stop to take photos of us, or how happy it made everybody. All night long, everywhere we went, people were smiling, waving, and pulling out their phones. At the Chinatown gate, a group of guys stopped to take photos of us, and when I offered to let them try the pumpkin heads on, they had an absolute blast. There happened to be exactly five of them, and we had exactly five pumpkin heads. That photo might be my favourite of the whole night.
My point is, budget for this too. A pumpkin head photoshoot in public is not a quick in-and-out mission, because the public becomes part of it. That ended up being the best part.
The Bard & Banker story, or, always ask first
The Bard & Banker was the stop I wanted most, and it very nearly didn't happen. It was a busy Saturday night, the place was packed, there was a lineup, and I was not about to wheel a cart of pumpkins through the door and start snapping photos. So I left the pumpkins and the cart outside, went in on my own, and politely asked if we could take photos for a couple of minutes in their front foyer. I said we would be very quick, respectful, and out of their way. The hostess said yes, and we got this shot.
We tagged them when we posted it, and they liked it so much they asked if they could have the photo to put on their own socials. It's on their Instagram feed now. That whole exchange is a lesson I keep relearning: ask first, be quick, be respectful, and share the good stuff back, and people will surprise you with how generous they are.
What I would do differently
- Foam in the top of the pumpkin. The stem bump bruise was real. A little cushion changes the whole night.
- Scoop even more aggressively (except at the stem). The weight sneaks up on your neck over hours.
- Bring a third human. Tripod and timer works, a photographer is better.
- Protect the stems at every step. Cutting, transporting, storing. They are fragile and they make the look.
- Two hands, every time. One quick grab out of the cart split a face, and we finished the night with four heads.
The space between wanting and doing
This is the part Living Vicariously actually exists for, so let me slow down on it. Crossing the space between wanting to do a thing and doing it is never one big leap. It's micro decisions. The first one was just saying yes, I want to do this. That one decision led straight to the next ones... what am I going to need to pull this off, and do I actually have the time? And then came the leap itself. Yes, it asks you to step outside your comfort zone. Carving a pumpkin into a helmet, putting it on your head, and walking into public spaces is not exactly conventional. The fun outweighed all of it, by a lot.
The total cost of entry, by the way, was six pumpkins, two dollar store toques, a camping cart I already owned, and one Saturday. It was never about money or gear.
And I know the interest is real, because the response to the photos has been wild. At the time of publishing this, the Facebook post alone is sitting at 9,700 engagements... 796 reactions, 79 comments, 52 shares from people passing it along, and over 8,600 clicks from people going through the photos one by one. That's thousands of people stopping to look at two people in pumpkin heads. And comment after comment is some version of "I've always wanted to do that." People are curious. People are sitting in the exact wanting spot I was sitting in. So if that's you, there's nothing stopping you from doing your own version... an afternoon of carving, an evening of wandering your own town, and a little bit of fun that people will be talking about for weeks.
The full set of photos from the night is on Facebook and on Instagram.
So consider this your sign. What's the thing you've been watching other people do, that you keep thinking about? Go do your version of it. And if you do, I want to hear about it.
#LivingVicariously #VictoriaBC #yyj
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