Wedding in MetroWest Boston, MA- Kay & Brian

Trinitarian Congregational Church + The Wayside Inn, Sudbury, MA

Kay and Brain’s wedding day will always be one I remember. Not just because it was beautiful, but because it was personal in every possible way. Kay is my cousin, and we’ve been close our whole lives. Getting to photograph her wedding felt like the most special full-circle moment.

After taking their engagement photos on the Jersey shore, I knew they would show up for these photos and boy was I right!

Their day started in MetroWest Boston at Trinitarian Congregational Church in Wayland, Massachusetts, with plans to take photos later at Longfellow’s Wayside Inn in Sudbury. The forecast called for nonstop rain, so we prepared for whatever the day would bring.

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Getting Ready and the First Look

We started the morning with getting ready photos, surrounded by laughter, hairspray, and the sound of rain outside. There’s always this mix of calm and excitement during that part of the day. Kay was so relaxed and happy, surrounded by people who love her most.

The guys were the ultimate hype club, giving Brian so much confidence and helping him to prepare to marry the love of his life!

Their first look took place in the church atrium. It’s a bright space filled with natural light, and even though it was pouring outside, it felt peaceful in there. The moment Kay and Brain saw each other, everything slowed down. They both just smiled and breathed, and it was clear how much they mean to each other.

The invitations were beautifully designed by Elise, one of the bridesmaids and they truly complimented a other details these two chose for their day. If you’re looking for a stationer for your wedding, look no further than Elise by Design.

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The Dress and the Veil

One of the most meaningful parts of the day was what Kay wore. She had tried on other wedding dresses but never felt completely right in any of them. Then she tried on her mom’s dress, and it instantly felt perfect. It suited her so beautifully, and it carried so much history and love.

She paired it with my wedding veil, which made it even more special. I was so honored when she asked to wear it. Seeing her walk around in her mom’s dress and my veil felt like the generations of our family were woven right into her day. It was simple and elegant and felt entirely her.

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When the Rain Stopped

All morning, the radar showed rain for the rest of the day. We were trying to decide if we’d need to change plans for photos, and then something incredible happened. The minute it was time to leave for portraits at the Wayside Inn, the sky cleared. It was still raining as we drove, but when we arrived, the air was calm and clear.

We had the exact window of time we needed to take all their couple and bridal party photos. The light was soft, everything looked freshly washed from the rain, and everyone was in such good spirits. As soon as we finished and started driving back to the church, the rain started again. My grandpa even took a screenshot of the weather radar that showed a pocket of clear sky right over Sudbury. It felt like one of those moments where you can just see God’s hand in the details.

It was so special to take their portraits at the Wayside Inn, a place we’ve been going too with Grandpa ever since we were kids for every special occasion and birthday. To say it’s a Rideout favorite would be an understatement.

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The Yellow Cadillac

For portraits, we brought out my great-grandparents’ yellow Cadillac. It’s been in our family for years and only comes out for special occasions. My grandpa loves driving it, and he couldn’t have been happier to play chauffeur that day.

The Cadillac has a lot of history for us, so seeing it parked at the Wayside Inn with Kay and Brain beside it felt really meaningful. It tied together the old and the new in the sweetest way. The bridal party had so much fun with it too — they were laughing, cheering, and celebrating even between shots. Many of them are friends I grew up with, which made everything even more fun.

The Wayside Inn was the perfect spot for photos. It has this quiet charm with gardens, stone paths, and the kind of New England scenery that never goes out of style. After all the rain, everything looked lush and full of life.

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Ceremony and Celebration

Back at Trinitarian, the rain had started again, but everyone was in high spirits. The ceremony was simple and full of joy. The lighting inside the church made everything feel cozy and warm, and it was special to see so many familiar faces in one place.

After the ceremony, we took family photos inside while the rain kept falling outside. Then came one of my favorite parts of the day. Kay and Brain changed into outfits made from African fabric that Kay’s sister Heidi had sewn. Kay grew up in West Africa, and Brain is from Zambia, so the outfits were a beautiful way to honor both of their backgrounds. Many guests also wore African prints, which made the whole room look vibrant and full of color.

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Cakes and Dancing

At the reception, every table had its own cake that Kay had baked herself. Each one was different, and guests could visit other tables to try a new flavor. It felt like such a personal and creative touch, and very “Kay.”

Once the dancing started, the energy never dipped. Our great-aunt Ida, who’s known for being the life of the party, made sure of that. She had everyone laughing and dancing right along with her. It was one of those receptions where everyone was just fully present and having fun.

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The Goodbye

For their send-off, the whole family lined up outside with white hankies in hand — a Rideout family tradition. Our grandparents have always waved their hankies from the porch whenever someone leaves for a trip, so it felt right to end the night that way. Everyone waved and cheered as Kay and Brain headed off for their honeymoon, and it couldn’t have been a sweeter ending to such a meaningful day.

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A Favorite Kind of Day

Photographing weddings is always emotional, but when it’s someone you’ve grown up with, it hits a little deeper. This day was full of family, faith, and so much love. Watching the rain clear just when it needed to, seeing the Cadillac out again, and documenting two people I care about so much — it all felt like a gift.

Kay and Brain’s day was a reminder that even when things don’t go perfectly according to plan, they can still turn out better than you imagined.

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Words from the Bride

“Kira (and second-shooter husband Caden) is the best. Her flexibility, attention to detail (phones out of pockets, please!), and calm enthusiasm made pictures one of the best pieces of our wedding day. We had so much fun capturing special moments with her, and would ask her to take pictures for us again in a heartbeat!” -Kay