Jordans, Rooftop Vows, and a Cake Smash in Portland, Maine
Karen (she/her) and Sinclair (she/her) leaned into their shared love of art deco bars, lobster rolls, and low-stress vibes to create an elopement that felt like pure, unfiltered them. From a dapper suit to a vintage cake smash in the street, every part of the day reflected their connection, their values, and their style. They eloped in Portland, Maine, with photos by the talented From The Fountain. And yes, the Jordans were coordinated.
Why did you decide to elope instead of planning a traditional wedding?
We just wanted to celebrate our love without the pressure of organizing everything around everyone else’s schedules.
Our people are spread out all over the place, so logistically a big wedding was already going to be tough. Once we realized how complicated it would be to get everyone in the same place, we had this lightbulb moment like, “Wait… what if we just did this our way?” And after that, everything just fell into place. No stress or endless to-do lists.
What were some of your favorite moments from the day?
Sinclair: Walking hand in hand through the cobblestone alleys after our City Hall ceremony felt straight out of a fairytale. People were congratulating us on the street, and Karen somehow made heels on cobblestone look effortless.
Karen: Watching Sinclair get her portraits taken on the steps of City Hall melted me. And of course, smashing our cake and licking frosting off each other’s noses will forever be a top memory.
You said your vows on a rooftop? Tell us more.
Yes! We snuck up to the top of a parking garage for some privacy and views. We wrote a few notes in our phones but mostly just spoke from the heart. It was spontaneous and sweet… and then security showed up. But they were kind enough to let us finish before we had to leave.
Let’s talk outfits. How did you decide on your looks?
We didn’t go the high-end bridal route. Instead we searched online until we found looks that felt like us. I wore a dapper white button-up with black pants. Karen had this playful white dress with sheer floral fabric. And we both wore Jordans, because of course we did. We even share the same shoe size.
What role did your vendors play in bringing this day to life?
Karen: I’d been saving inspiration forever, so I had a clear vision. Our vintage-style heart cake was made with love by Meadow Sweet Bakery, and it turned out exactly how we imagined. Emily (the owner) is a vendor at the restaurant I work at, and she was just so kind and professional. The flavor, the look, she nailed it from a reference photo.
Sinclair: We’re big food people, and The High Roller is our go-to for lobster rolls in Portland. It was the perfect post-ceremony stop. And we ended the night at Via Vecchia for cocktails. Their art deco interiors matched the aesthetic we love. The staff was incredible and made space for us last minute.
And we have to shout out From The Fountain, our photographer. Rebekah helped us prep, made us feel relaxed, and her candid style was exactly what we were drawn to. The photos came out so beautiful we barely recognized ourselves at first. She’s the real deal.
Any advice for other couples thinking about eloping?
Whatever route you choose, make sure it helps you feel the most present and authentic. Eloping let us focus completely on each other. We weren’t worried about timelines or expectations at all.
Photography by From The Fountain
Cake Meadow Sweet Bakery
