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A summer reunion at Wintergreen – and what makes relaxed extended family photos work

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I’m obsessed with stories of family, creativity, and simple joys.  A nostalgia nerd, writer, wife, and mom of 3, I believe life’s most fun when you’re dreaming big and savoring small.

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When your family scatters across states and schedules, finding a window where everyone lands in the same place is its own kind of miracle. Last summer, a family made that happen at Wintergreen resort in Virginia and reached out about making some relaxed extended family photos while they were all together.

Because reunions are scheduled and locked in, we have to go with what nature gives us. This night called for rain in the evening of their session, but we crossed our fingers and decided to roll with it. To beat the rain as best we could, I decided to start with portraits at a nearby field just down the road from the home they were renting. We had space to get playful and make photos of all different groupings under the overcast skies. Just when were were finishing up and walking to our cars, it started raining.

Our plan was always to go back to the house and unwind while they cooked dinner and played their favorite card games, which worked out great. And even though it was cloudy and pretty dark inside between the weather and their wooded property, we let the vibes carry us.

The kitchen filled up, they poured a few drinks, the cards came out, some kids even started dancing to Ganganm style. It was full of personality, love, and honesty – exactly the kinds of in-between photos you treasure.

Later, the sky cleared enough for us to slip out to the back deck for a few more group photos and breakdowns to end our time.

summer extended family photos in virginia
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relaxed extended family photos in wintergreen resort
activity ideas for extended family photos
extended family photos at wintergreen resort

What makes relaxed extended family photos like this one work is how naturally they move.

There’s a loose shape to the timeline, and within that shape, a lot can happen. The combination of classic portraits and relaxed family time makes for a really special, storytelling collection of images that speak to who a family is, not just a performance of it.

extended family photos with 5 adult siblings

Tips for relaxed extended family photos

Extended family photos come with a particular kind of pressure that smaller family sessions don’t. More people, more opinions, more logistics – and often, real anxiety about whether it’s all going to feel stiff or staged or like a lineup of people who were told to smile at the same time and now look like they’re in pain.

The goal is to capture what it actually feels like when your people are all in the same place – a rare and precious thing.

Here’s a few things that tend to make relaxed extended family sessions (the one I just shared!) feel good rather than grueling:

1.Where you already are is usually the right location.

Whether it’s a reunion at a cabin, a family farm, or a vacation rental — these spaces already have meaning built into them. The place where everyone has gathered is part of the story, and leaning into it almost always produces more interesting images than driving somewhere scenic would. And just like in regular family sessions, it always lends itself to more ease (not rushing to get 15 people out the door?!) and more relaxed results.

2. Plan an activity you’d do anyway.

When people have something familiar to focus on, they relax more than when they’re standing there looking at a camera pointed at their faces. A meal, a card game, fishing off a dock, playing croquet in the yard, a tradition the family already has – all of it lends to a more natural interaction. You’re not performing for the camera; you’re just doing the thing you do together, and I’m there to artistically document it.

3. Expect a mix of moments and group shots.

Some of the most meaningful extended family images are quieter ones — two siblings catching up on the porch, a grandparent watching the kids play, cousins disappearing to feed the chickens. We’ll always check the big group portraits, breakdowns of cousins and grandparents and each family unit – that’s a given. But a session with a larger group has more of those small moments to find, too, and I’m looking for them alongside the bigger group portraits throughout.

4. Let go of conditions being perfect.

Someone will show up in an outfit that feels off. A kid will have a meltdown at an inopportune time. The weather will have its own ideas. None of it is fatal to a good session. It’s personality and reality – all of which we want more of, right? It’s part of a story that has roots. The photos will be meaningful and beautiful, wholly true and wholly you.


Planning a Reunion or Extended Family Session in Central Virginia

The Wintergreen and Shenandoah valley area has so many great options for large families to gather. I photograph extended families all over central Virginia, wherever the reunion happens to land.

If your group is mostly adults, or a mix of adults and kids, or multigenerational in a way that makes logistics feel complicated – I’m here for it and love it all. Family is family at any size and it means so much to me to captures all the ways it can look magnificently different.

You can read more about how I approach extended family sessions here, or reach out to talk through the specifics of your group.

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Hi, I'm Leah -
lifestyle family photographer, writer, & educator.

I’m  one of the first to meet your newborn baby, the one who won't judge your clothes baskets and unmade beds, and the one who can capture the way your husband looks at you with a twinkle in his eye after 12 years of marriage.  My life's work is about honoring people and telling stories.

I believe art has the power to light up the world in dark places, starting at home. 

I'm a mom of 3 who loves mornings and words. I rely heavily on black coffee and a sense of humor.

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