Some couples just have a story that you can't stop thinking about.
Ashley and Tripp are absolutely one of those couples. From matching on Tinder after years of crossing paths in Rhode Island as teenagers, to quitting their jobs to travel the country for six months, to getting engaged in New Zealand while geocaching by a glacier... they are genuinely one of the most adventurous, whimsical, and fully alive pairs I've ever had the privilege to photograph.
Their wedding on May 25th, 2025 was everything you'd hope for from a couple like this: intimate, joyful, full of personal details, and deeply rooted in love and celebration. Held on a private property in New London County, Connecticut, the entire day had this warm, familiar energy.
It was a cloudy spring day, but the soft diffused light gave everything this romantic, dreamy quality. And when that sunset finally broke through right before dark? We grabbed it. Here's how their whimsical backyard Connecticut wedding unfolded.
getting ready and an emotional first look
The Day Started with
Ashley getting ready surrounded by her bridesmaids. Her dress was absolutely stunning, floral embellishments across a sweetheart neckline, a flowing skirt, and a long floor-length veil that moved like a dream. But what really made her look unforgettable was her hair: braids woven throughout with blue tinsel catching the light. It was whimsical, unexpected, and so completely Ashley.
Before the ceremony,
Ashley and Tripp opted for a private first look. I am always such an advocate for first looks... especially for couples who want a moment that's just theirs before the day becomes a beautiful blur. They saw each other, exchanged private vows, and both of them got emotional in the best way. It set the tone for everything that followed: intentional, present, and deeply connected.
Tripp wore a light tan suit that perfectly complemented the whimsical spring vibe, and the groomsmen looked sharp in deep blue. The bridesmaids wore different shades of teal — some in dresses, some in suits — which not only looked incredible in photos but also felt so reflective of who Ashley and Tripp are as a couple. Inclusive, thoughtful, and unapologetically themselves.
Portraits by the Lavender Blooms
One of the most gorgeous spots on the property was a bed of lavender flowers in full bloom, soft purples against lush green, with just enough wildness to feel organic and romantic. We did the majority of the wedding party portraits and couples portraits here before the ceremony, and the light was soft and even thanks to the cloud cover. Sometimes overcast spring days give you the dreamiest, most flattering light, and this was absolutely one of those days.
The wedding party was such a vibe... five groomsmen, six bridesmaids, all of them completely present and having the best time. There was laughter, there were candid moments, and everyone just seemed genuinely thrilled to be there celebrating Ashley and Tripp. That kind of energy makes my job so easy.
A Backyard Ceremony Full of Love and Surprises
At 5:00pm, guests gathered on the lawn for the ceremony, white folding chairs arranged in rows, a backdrop of towering trees, and 125 people who had come from near and far to witness this moment. There's something so grounding about a backyard wedding. It's intimate in a way that a traditional venue just can't replicate. You're literally on the land that belongs to someone you love, surrounded by people who matter, with no pressure to perform for anyone but each other.
And then came one of my favorite surprises of the entire day: instead of traditional flower girls, each of the groomsmen walked down the aisle and surprised the guests by pulling flowers out of their suit pockets. It was such a playful, unexpected touch... classic Ashley and Tripp. The crowd loved it.
When Ashley walked down the aisle, you could feel the shift in energy. Tripp's face said everything. The ceremony itself was beautiful, heartfelt, emotional, and so clearly about the two of them and the life they've already built together. When they kissed as a married couple for the first time, the entire lawn erupted in cheers
Cocktail Hour and Candid Family Moments
Immediately following the ceremony,
we grabbed quick family portraits while guests moved into cocktail hour on the patio. This is always one of my favorite parts of a wedding timeline, the ceremony is over, the formal portraits are done, and everyone just exhales. The cocktail hour had such a relaxed, celebratory energy.
And then Ashley and Tripp pulled another surprise: they appeared on the balcony above the patio, waving down to their guests before coming down for candid group photos with everyone. It was such a fun, spontaneous moment, and ended up being some of my favorite photos of the day.
A Tented Reception Full of Personal Touches
The reception was held in a large white Sperry Tent set up across from the ceremony lawn. As the evening went on and the temperature dropped, the zippered walls came down, creating this cozy, glowing atmosphere lit by strings of warm bulbs. It felt magical.
One of the details that absolutely stopped me in my tracks was the seating chart: hand-painted with illustrations of national parks that Ashley and Tripp had visited together. Each table was named after a different park, and it was such a beautiful representation of their love for travel and adventure. These are the kinds of personal touches that make a wedding feel like a true reflection of the couple, not just a pretty event, but a story.
The night began with the wedding party grand entrances, followed by Ashley and Tripp's first dance. Then came the father-daughter dance, toasts from family members, and a mother-son dance. Everything flowed beautifully, and you could feel how much thought had gone into every moment.
Chasing the Sunset (and Actually Catching It)
It had been cloudy all day, so I wasn't expecting much of a sunset. But right before the sky went completely dark, we got this brief, beautiful window of golden light. I grabbed Ashley and Tripp, and we ran outside for a quick sunset portrait session. Just the two of them, the glow of the fading light, and a few stolen minutes away from the party.
These are the moments I live for as a wedding photographer. The unplanned, fleeting, grab it while you can moments that end up being some of the most stunning images in the entire gallery. The light was soft and warm and they were both just glowing. It was perfect.
A Dance Floor That Went Off
After dinner and a private cake cutting with more family toasts, the dance floor officially opened... and it did not disappoint. The energy was absolutely electric. Guests were dancing with glowing light sticks, the tent was alive with laughter and music, and Ashley and Tripp were right in the center of it all, completely in their element.
I loved photographing the dance floor at this wedding. The glow sticks added such a fun, colorful element to the images, and the movement and joy on everyone's faces was just contagious. This is what a wedding reception should feel like!!
What Made Ashley and Tripp's Wedding So Special
This was a wedding that was deeply inclusive. Members of the LGBTQIA+ community were part of the wedding party and among the guests, and the entire day radiated acceptance, love, and celebration of everyone exactly as they are. Every detail felt like a love letter to the life they've built and the people they've brought along for the ride.
It wasn't just about the aesthetic, though the whimsical details, the lavender portraits, and the tented reception were all stunning. It was about the intentionality behind every choice.
And that's what I think made this wedding so memorable to photograph: it was unapologetically them. From the first look to the dance floor, everything felt authentic. Ashley and Tripp didn't just throw a beautiful party, they created an experience that reflected who they are as a couple, and they invited 125 people to be part of it.
I'm based in Newport, Rhode Island, but I photograph weddings throughout New England and beyond!
If you're planning an intimate wedding, a backyard celebration, or a grand wedding celebration and you're looking for a photographer who will document your day with intention, artistry, and a whole lot of heart, I'd love to hear from you.