Annual Family Photos in Weston: Six Years of Chaos, Connection, and Chicken Coops
Golden hour light was streaming through the trees on their Weston property, backlighting the ferns and what was left of the fall color. It was one of those late November afternoons where the weather does exactly what you hoped it would, and you spend the whole session quietly grateful you didn’t have to explain to everyone why their fingers are numb.
This was their sixth year in a row doing family photos with me. Six years. Which means I’ve watched their kids grow from toddlers who could barely walk on those log stumps by the river to kids who now race across them without a second thought.
The Chicken Coop Tradition
Every year, we start the same way: a photo in front of the chicken coop for their Christmas card. It’s the one “posed” shot we do, and even then, things rarely go according to plan.
One year, a chicken took off mid-flight in one of the kids’ hands. Another year, their dog Taco photobombed the whole thing. And you know what? Those ended up being some of their favorite photos from those sessions.
Because here’s what this family gets that a lot of families don’t: real life is messy. And trying to fight that mess, trying to force everyone to smile perfectly and stand still and cooperate, just creates stress. It takes you out of the moment instead of putting you in it.
So we get that one “official” photo out of the way, and then we just… go. We follow the kids around their property. We end up wherever they lead us.
What It Looks Like When Everyone’s Actually Present
This year, they showed me their special trees. There’s one where they hide things around Christmas time. Another one that’s their favorite to jump off of.
The mom has planted native plants all over the property. (As a nature nerd myself, this always makes me unreasonably happy.) Earlier this spring, they even had me come photograph a Great Horned Owl nest in their backyard—two owl chicks just hanging out in a tree like it was totally normal to have owls nesting on your Weston property.
But what really struck me this particular session was a quiet moment near the end. The sun was setting, and this incredible light was hitting their house. The parents had already sent the kids inside—which, as a dad of small kids myself, I know requires a level of trust that the older ones will keep the younger ones safe. And for just a minute, it was the two of them. Looking out over their property. Not posing, not performing, just… there, together. With two little kids at home, those moments are rare. I felt kind of honored to capture it.
Why Annual Family Photos Actually Matter
Here’s the thing about doing photos every year: you end up with something you can’t recreate later. This family can now make an album showing six years of growth. Six years of their kids getting taller, their smiles changing, their personalities emerging. Flipping through those pages, you can see the whole story. And here’s what I’m guilty of myself: we have photos of our daughter all over our walls. Our son? Not so much. It’s easy to take a million photos of one kid and then realize years later that you have almost none of another. Annual family photos—whether you do them with me or someone else—solve that problem. Everyone gets documented. Everyone’s growth gets honored. Nobody gets left out of the visual record of your family.
The Weston, Massachusetts Advantage
I love photographing families on their own properties in Weston. The light is different in every backyard. The way kids interact with their own space—the trees they’ve climbed a hundred times, the stumps they’ve learned to balance on, the chicken coops they visit every day—it’s just different than bringing them somewhere unfamiliar. This family’s property, with the river and the golden light and the native plants and apparently the owls, gave us everything we needed. But honestly, it would have worked anywhere. Because what made these photos work wasn’t the location. It was the fact that everyone was actually there. Present. Not trying to control anything or make anyone cooperate. Just being together. With a family of four, those moments are rare. A photo session can be an excuse to create one.
A Note on Annual Sessions
If you’re a Weston, Massachusetts family thinking about making photos an annual tradition, I have a loyalty program for families who book year after year. You get a special rate, and perks like bonus mini-sessions throughout the year. Like when you have owl chicks in your backyard and want someone to document it. Just saying. If that sounds like something you’d be into, you can learn more about annual family photos and my approach here.
