There’s a moment on Halloween night that I think about a lot. It’s not the costumes or the candy (though let’s be honest, I still eat more of my kids’ candy than I should). It’s the moment when a grandparent opens their front door and a grandkid is standing there in some ridiculous costume, beaming. The grandparent’s face does this thing that cameras were invented for.
I’ve been filming families long enough to know that the best intergenerational moments aren’t the big planned events. They’re the small, slightly chaotic ones. And Halloween is pure chaos in the best way.
Carving pumpkins together is underrated. Not because the pumpkin turns out well (it never does when a five-year-old is involved) but because of the conversation that happens while everyone’s elbow-deep in pumpkin guts. Grandparents tell stories about their own Halloweens. The costumes they made out of nothing. The neighborhoods they trick-or-treated in. The year something went hilariously wrong. A pumpkin is just an excuse to sit at the same table and talk.
Let grandparents pick the costume. Or at least contribute to it. I know a family where the grandmother makes one piece of each grandchild’s costume every year. A cape, a hat, a pair of wings. The kids could buy better versions at the store, obviously. That’s not the point. The point is that a seven-year-old is running around on Halloween wearing something Grandma made with her hands, and that becomes the story.
Trick-or-treat together. Walk the neighborhood. Let Grandpa carry the extra bag. Let Grandma be the one who checks which houses have the good candy. It’s slower. It’s better. Grandparents on the sidewalk with flashlights and grandkids sprinting from door to door is one of those simple images that sticks.
Watch something “scary” together. Scary in quotes because the right movie depends on the age of everyone involved. For little kids, it’s Hocus Pocus. For bigger kids, maybe Ghostbusters. For teenagers, let Grandma pick something actually scary and watch her handle it better than everyone else in the room.
The thing about holidays with grandparents is that the grandparents remember doing this exact thing 40 or 50 years ago. And the grandkids won’t realize it yet, but they’re building memories they’ll carry just as long. Halloween is just the wrapper. The real treat is the time.
(I promise that’s the only candy pun.)
If you want to preserve the way your family spends time together, not just on Halloween but every day, Heritage Films captures those stories and those voices on film. Because the costumes change every year, but the people wearing them are irreplaceable.


