At a St. Patrick’s Day party, she and Matt unexpectedly ran into each other, and “that same easy feeling from years ago rushed right back,” she remembers. Their first date soon followed . . . and lasted six hours. “Looking back, I think I was subconsciously hoping for the day Allyson would come back into my life,” Matt says.

Eight-and-a-half years later, he proposed during one of their usual coffee walks through Central Park, with both families waiting nearby to surprise Allyson. The day concluded, somewhat accidentally, at a performance of Wicked. “We love Central Park, we love our people, and I love Broadway,” Allyson says. “It was perfect, even though the Broadway part wasn’t planned!”

For their June 27, 2026 wedding, the couple returned to Michigan, choosing Bay Harbor, where Allyson’s grandparents have had a home since the ’90s. “It’s full of memories old and new, and we wanted our wedding weekend to feel like an extension of that,” she says.

The setting may have been Lake Michigan, but the couple looked to their life in Manhattan for the mood. Bemelmans, The Nines, Minetta Tavern, Waverly Inn, and other favorite downtown haunts filled their inspiration boards, eventually leading to a clear directive: an old-Hollywood New York supper club on the water.

OTM Directory Planner Ann Travis Events led coordination and design, working with Bloom on florals and HMR on décor to bring those seemingly disparate worlds together.

The weekend began with a private family ceremony, for which Allyson surprised her mother by wearing the satin, off-the-shoulder wedding dress she had worn in 1986. “It fit perfectly,” Allyson says. Knowing how much her mother loved the dress—and thinking of the marriage her parents shared before her father’s passing—made wearing it especially meaningful.

On the wedding morning, Allyson again reached into her family history, getting ready in the silk slip and robe her mother had worn on her own wedding day. When it came to the main dress, however, she wanted something entirely her own. Most important was movement: She imagined a skirt that would move “like water swirling around stones in a lake.”

After stumbling upon House of Gilles in a Vogue Bridal Week story, Allyson added a last-minute appointment to a schedule already filled with visits to major Manhattan bridal houses. At the atelier, she found the Brittany, made in luminous crepe-back satin with a hand-draped sweetheart neckline, dropped basque waist, and billowing A-line skirt. “It captured Gilles’s signature: structure on the inside, fluidity and weightless movement on the outside, which is quite literally exactly what I’d envisioned,” she says. “It truly was a piece of art.”

A cascading House of Gilles Chantilly-lace veil added even more movement. Face by Nertila created Allyson’s beauty look, while her jewelry carried the family story forward: diamond studs from Matt, the gold-and-diamond locket her father had given her mother on their wedding day, and a tennis bracelet from her mother. A pin containing three family heirloom charms, gifted by her sister, was fastened to her bouquet.

Matt went custom too, wearing a black silk-wool Suitsupply tuxedo with an espresso-brown houndstooth lining. Their initials were embroidered inside in gold, their wedding date appeared beneath the collar, and he wore cuff links passed down through Allyson’s family.

The ceremony took place on the beach, where a long chartreuse aisle led toward a matching fabric-draped arch overflowing with flowers against the turquoise waters of Lake Michigan. Allyson’s mother walked her down the aisle, while a string trio performed songs by artists the couple had seen in concert together. “The moment I took my first step down the aisle, I felt like I was floating,” Allyson remembers. “Then Matt came into focus, beaming at me, and honestly, he took my breath away.”

After recessing to “December, 1963,” the party began in earnest. Cocktail hour introduced the supper-club mood with a jazz string quartet, Champagne coupes garnished with maraschino cherries, and a shrimp cocktail display by Vernales. Then, guests passed through a “palm portal” and into the tent.

Inside, zig-zag drapery swept across the ceiling, fabric walls shifted in the lake breeze, and sconces cast a low glow over tables layered with eclectic linens, moody lamps, and richly colored flowers. Palms framed a fringed bar, while Chateau Band performed from a 1920s-inspired bandstand with tassels, swooping drapery, a hand-painted botanical backdrop, marquee bulbs, and shell-shaped footlights. Grey and Cake created the paper details, and Simply Sweet by Jessica made the wedding cakes—including a 90-pound chocolate cake layered with vanilla buttercream and raspberry filling.

Allyson and Matt opened the dance floor with “Mango Tree” by Zac Brown Band and Sara Bareilles, a jazzy swing song they had danced to in their kitchen for years. “Everyone assumed we’d taken lessons,” Allyson says. “But really, we just love swing dancing and happen to be pretty good at it!”

From there, Chateau Band turned the evening into what the couple describes as something closer to a concert than a wedding reception. Allyson and Matt joined them onstage for “Jessie’s Girl,” only for the band to surprise the groom by swapping the lyric for “Matthew’s Girl.” There was crowd surfing, a mid-air kiss, a fog machine, and another round of “December, 1963” onstage with the flower girls.

Photographers Kim and Travis of Calenrose captured it all—including an impromptu, martini-fueled portrait session in the lounge midway through the evening. Kelly LaFleur Films also documented the weekend on film, preserving everything from the lakeside ceremony to the energy of the dance floor.

Allyson had planned to change for the after-party but accidentally left her second look behind. In the end, it hardly mattered. “I never wanted to take my gown off, and I didn’t want to leave the party to change,” she says. “It was made for dancing, and the gown really had a moment of its own on the dance floor.”

After the reception, one friend promptly jumped into the bay wearing nothing but his boxers and bow tie, and everyone continued to a nearby distillery for Jet’s Pizza, ranch, and cocktails named after the couple’s parents.