I’m Linda Sobolewski, a senior photographer at Hammonasset Beach in Madison, specializing in high school senior, family, maternity, and newborn photography on the Connecticut shoreline. One of my favorite things about this job is getting to know each senior throughout their session. Lily’s was one of those sessions I didn’t want to end.

Lily and her family are still fairly new to Connecticut. There was something really special about spending an evening with her at Hammonasset Beach while she gets to know her new home. By the end of the session, it felt like we’d known each other for years.

Why I Loved Being Lily’s Hammonasset Beach Senior Photographer

Lily was so much fun to be with. She’s funny, easygoing, and honestly one of the most natural seniors I’ve photographed in a while. I barely had to direct her. She moved, laughed, and posed so easily. Most of my favorite images from her gallery happened between the poses I actually planned.

That’s always the goal with a Hammonasset Beach senior session: create enough space for a senior to just be herself, and let the location and the light do the rest.

Two Dresses Made Lily’s Gallery Feel Like a Storybook

Lily’s first outfit was the kind of dress you don’t forget. A soft pink, tiered mini dress with a ruffled skirt, paired with a bouquet of pink and white flowers. It was absolutely stunning and Lily looked gorgeous in it. We jokingly, lovingly started calling it the cupcake dress, and honestly, it fits. We photographed this look just before we made our way down to the beach.

For her second look, Lily changed into a long, flowing blue dress and walked straight into the water without a second thought. I always love a long, flowy dress for the beach and the water. It moves so beautifully and photographs like nothing else. It was playful and stunning all at once, and was exactly the kind of unexpected moment that makes a Hammonasset Beach session feel one of a kind.

Her Whole Family Joined Us at Hammonasset Beach

Sometimes a senior session ends with just the senior, and sometimes the whole family joins us at the end, which is exactly what happened with Lily. Her family met us at the beach, and we got to capture a few images of all of them together. I wish every family dressed the way this one did. They were coordinated without looking matchy, and it was clear they’re just beautiful, fun loving people. Getting to photograph the whole family together, right there at Hammonasset Beach, was the perfect way to close out Lily’s session.

To Lily,

Thank you for bringing so much joy and so much fun to your senior session. Watching you settle into Connecticut and finding your own home right here at Hammonasset Beach was such a gift to be part of. I wish you nothing but the best as you begin this next chapter. xo

Senior Session FAQ

How many outfits should I bring?

I always recommend at least two, like Lily did. Going from a shorter, playful look to something long and flowy for the water gave her gallery so much range in just one evening.

When is the best time to book a Hammonasset Beach session?

I book on a rolling basis, but the golden hour sunset spots go first, especially in late spring and summer. The earlier you reach out, the more flexibility you’ll have with dates.

Many of my clients ask me, “When is the best time of year for senior pictures?”. Most of my seniors love late July, August, or early September. However, my personal favorite months are late September and October. The air is crisper, and the humidity and bugs have calmed down. Additionally, the chance of pop-up thunderstorms drops way down, and the light turns extra golden. This makes everything feel dreamy and effortless.

If you’re looking for a Hammonasset Beach senior photographer, I’d love to help you plan a session that’s just as fun and just as you as Lily’s turned out to be. Whether you’re dreaming of walking into the water in your favorite dress or ending the evening with a quiet moment at sunset, we’ll create a gallery you’ll love for years to come.