Documenting Generations: An Extended Family Photo Session at Historic Tuckahoe

Everyone Is Finally Together

If coordinating annual photos with your immediate family feels like a feat, planning extended family portraits can feel nearly impossible.

Distance. Work schedules. School calendars. Age ranges that span toddlers to grandparents. It’s no small task to gather multiple generations in one place at one time.

And yet — when it does happen — it’s rare and deeply meaningful.

Why wouldn’t you want to preserve a moment like that?

Photographing Layers of Generations

What a gift it is to document families as all the generations together. There is something profoundly moving about documenting a family with all its layers present.

As a mother myself, I treasure the photos I have of my parents and the photos I have of my children with my parents.

And the cousin crew? The laughter, the chaos, the energy of them all together — it’s a kind of magic. Yes, gathering children of all ages for portraits requires a little patience. But that joyful, barely-contained energy is part of the story. It’s real. It’s worth remembering.

Choosing a Location for Extended Family Photos

When planning an extended family session, location matters — and ease is always my first consideration.

For this session, we photographed at Historic Tuckahoe, a timeless Richmond setting with beautiful variety in a relatively walkable space. It offers room for a large “everyone together” portrait, while also providing intimate corners for smaller groupings.

Just as important? It’s easy to access and navigate…which is a huge consideration for grandparents (and toddlers!).

If your family is gathering at a rental home or a meaningful property, we can absolutely plan around that. We’ll consider the best light, accessible areas, and how to create visual variety without making the experience feel like a production.

What an Extended Family Session Actually Feels Like

Extended family sessions are a thoughtful balance. We capture the must-have portraits — the full group, individual families, siblings, grandparents with grandchildren — and we do so efficiently, with intention. We’ll plan a simple shot list ahead of time so priorities are clear and no one feels stressed in the moment.

But beyond the formal groupings, I’m watching for all the gold that’s happening in between – the grandparents adoring their grandchildren. The siblings who haven’t seen each other in months and reminisce about silly stories from childhood. The cousins who just can’t stop giggling.

The goal is a relaxed, steady flow that allows children (and grandparents) to simply be themselves. Because when everyone is finally together, I don’t want you worrying about the schedule. I want you to savor it.

Images That Become Part of Your Family History

It’s a reality none of us like to dwell on — gathering all the generations won’t always be possible.

Time moves forward. Children grow. Parents age.

Freezing even a small piece of that timeline — your children with your parents, cousins still playing tag, siblings shoulder-to-shoulder — it’s a fleeting gift.

One day, those cousins will look back at these images and see more than smiling faces. They’ll see the roots of who they are. They’ll see where they come from.

And for you? These photographs will only grow sweeter and more sacred with time.

This is legacy work. Not just portraits for the year — but part of your family’s history, preserved with care.

I’m Amy Cherry—a newborn and family photographer based in Charlottesville, VA who cares deeply about the little things. And I believe they should be savored and documented in all the chaos, the tenderness, and the in-between moments you don’t think to document but never want to forget. I’m here to help you hold onto it all.