Growing up in the country, Halloween wasn’t spooky season. It was gas-up-the-van-and-hope-you-hit-five-houses season. My brothers and I would pile in, dressed in whatever costume plastic and imagination could cobble together, and hit a handful of homes—each one separated by long stretches several minutes in the car.
Mama was our Halloween MVP. Daddy was usually still at work, so she’d load us up, snap our porch photos (every single year), and haul us from porch to porch like a one-woman candy Uber. We’d run up to Grandmama’s house first to see the massive jack-o’-lantern she always had on the front steps. I’m talking three feet high, the kind of pumpkin that made your eyes go wide. Granddaddy never said where he got them, but he was proud of them—standing back with a grin like he grew the thing himself.
Inside, Grandmama had gift bags waiting. Not just candy, but money and an RC Cola to boot. She made one for each grandkid, and you better believe I looked forward to those bags just as much as the candy from strangers. Because they weren’t just bags. They said, “I see you. You matter.” They were her quiet way of making each kid feel like the favorite.
We didn’t go to many houses, but we made it count. There was always candy-trading and brotherly bartering in the back seat afterward—“I’ll give you two Dum Dums for one Reese’s.” We learned early that Halloween wasn’t about who got the most. It was about making sure everyone had enough. That’s a lesson that stuck.
And then there was one Halloween—a game changer. My brother Sean and I spent the night at a friend’s house, and his mom drove us into town for real trick-or-treating. She was new to the area and didn’t quite know the “neighborhood norms,” so she just drove behind us slowly as we hit house after house. We filled up an entire pillowcase. I had never seen that much candy in one place that didn’t require a cashier.
That’s the kind of night I wanted my kids to have.
So when I missed Brighton’s first Halloween due to work, I made a vow right then—I wouldn’t miss another one.
Now, Halloween is the starting pistol for the holiday season in the Wood household. And we don’t take it lightly. We begin planning costumes in September. There’s chili in the Crockpot, hot cider in mugs, and pumpkins on the porch and inflated ghosts in the flowerbeds before you can say “full-size candy bar.”
We walk the neighborhood from sundown until our legs say no more. I carry the wagon, the jackets, and sometimes a lightsaber (if I’m a Jedi that year). Other years, it’s the Batman suit. The real one. My youngest still gives me that half-grin, half-awe look like he’s trying to figure out if I’m actually Bruce Wayne. Honestly? I don’t blame him.
We snap pictures on the front porch in the same spot every year. My wife makes sure of it. And while I wish I were better at capturing those moments, I’ve become better at living in them. I walk beside my kids and take mental videos—watching how they say thank you, how they trade candy with kindness, how they look out for each other’s favorites.
Now that we live in a sidewalk neighborhood, it’s not just about the candy haul. It’s about bumping into neighbors, catching up, walking slower, laughing together. It’s about doing the same thing with the same people until it becomes the thing you all look forward to.
My mom and stepdad come over now to hand out candy at our house while we trick-or-treat with the kids. They get to see the family they helped shape. It’s like planting a garden and finally getting to sit on the porch and admire the bloom.
This past year, I thought my oldest might be done with Halloween. But when I asked if he planned to go out, he said, “Of course. That’s family time.” I couldn’t have scripted it better if I tried.
Because here’s the truth: when your kids are small, you’re planting seeds. You’re tending the soil with traditions, presence, and consistency. As they grow, those seeds dig roots. And one day—when they’ve got kids of their own—you’ll look up and realize: the harvest has come.
It might look a little different. Maybe you’ll be invited to their house for Halloween chili. Maybe you’ll help hang the lights on one of their five Christmas trees. But you’ll know, deep down, they were watching all along.
Tradition matters. Togetherness matters more. But one without the other? That’s just a costume with no mask. A pumpkin with no candle.
So yes, we go all in. We eat the chili. Not because it’s efficient. Not because it’s convenient. But because it’s ours.
And if, someday, there’s a grandkid who hands me a Kit Kat and says, “This one’s for Grandaddy,” I’ll know:
The harvest I didn’t see was growing the whole time.
