Edward “Teddy” Kennedy III and Rose Esselstyn can never agree on exactly how they met, but they both remember the location. It was her first week of sophomore year after transferring in, and his first of junior year at Wesleyan University—and they were both in the Usdan dining hall. “I remember seeing her and waiting for her to put her dishes away so I could ‘run into her’ at the dish conveyor belt station,” Teddy says of their meeting in 2018. “She remembers it the other way around: She got up and followed me, and I said, ‘Are you following me?’ to which she replied, ‘Would it be okay if I were?’ After this, we had our first coffee date, and I knew in my heart that she was the one.”

Her version might be slightly better supported by evidence, as Rose had seen Teddy speak on a panel for first-year and transfer students like herself, where students from different backgrounds discussed their lives and lessons they’d learned. He had spoken about sailing and how wind alone is only one factor. “I lamented the loss of my grandfather and talked about turning a sailing career marked by last- and second-to-last-place finishes into a resounding success thanks to his direction,” Teddy recalls. “That summer, I won a championship and was grateful my grandfather was there to see it. This message echoed with Rose, who also shared a sense of family values, among those perseverance and a reverence for those who came before us.”

After dating for nearly seven years, the two got engaged on May 31, 2025, at Rose’s family’s historic farm in Claverack, New York. “I arranged for her family to join us and for mine to come up clandestinely so as not to alert her to their presence until the time was right,” Teddy says. “It was a rainy day, and I had to push back my planned ‘walk’ until the clouds broke. I also organized a surprise private dinner at the Klocke estate later that night to celebrate with our families.”

The couple’s wedding took place just over a year later on June 13, 2026, at 4 p.m. at the same location. The ceremony took place atop the Tank House Hill, overlooking the Catskills and the Hudson Valley, at a farm that has remained in Rose’s family for nearly 350 years across 11 generations.

At one point, the couple considered marrying in Hyannis Port. “But my love of the countryside—and the sense that the venue should be the bride’s choice—led us to the farm,” Teddy explains. “I have no doubt we’ll spend a lot of time in Hyannis Port though.”

Once the venue had been decided, Rose and Teddy jumped into planning. At first, it was harder than they both anticipated. “Rose has tremendous project management skills, which I wish I shared,” Teddy jokes. “I contributed by taking on ceremony design, seating charts, music, and lighting.”

In the months leading up to the wedding, Rose’s parents, Ted Esselstyn and Anne Bingham, devoted countless hours to planting, painting, and beautifying the farm. Ted also sketched the intertwining tulips that became the wedding emblem, appearing everywhere from the invitation suite to Teddy’s wedding band. “The easiest part of the process was that Rose and I had shared visions for the day from the beginning,” Teddy says. “The harder part was executing on that vision. Neither Rose nor I like superfluous details. We like things classic and simple.” The two worked with Amanda Serroukas for event planning and Main Course for catering.

Both Rose and Teddy worked with stylist Michael Smith on their wedding weekend wardrobes, and the bride reimagined her mother’s wedding dress for the rehearsal dinner. A welcome party followed later that evening at the Maker Cafe in Hudson, for which the bride changed into a dress by The Row paired with Jimmy Choo shoes.

For the wedding ceremony, Rose chose a dress by Oscar De La Renta, who dressed Jackie Kennedy in several custom looks throughout her life. The bride wore family heirlooms, including pearls from Teddy’s grandmother and sapphire jewelry gifted by Teddy and his mother.

Teddy wanted something classic and chose a morning coat. “It’s a traditional style worn by my great-grandfather, grandfather, and many uncles and great uncles,” he says. “It was an easy choice, especially for a countryside wedding.” He accessorized with a black-leather banded 1956 Omega Seamaster. “The Seamaster is understated and belonged to my grandfather,” Teddy notes. “My tie clip is an Amethyst set in platinum and gold, which belonged to my grandfather and is our shared birthstone.”

He finished his look off with mismatched “EMK” and “RFK” Cartier cufflinks. “Before my uncle Bobby Kennedy was lowered into his grave at Arlington, my grandfather took one of his own cufflinks and replaced it with one of his brothers, each now sharing a piece of the other. I remain in awe of my grandfather’s own perseverance, still speaking of visions of hope for the future, despite experiencing so much personal tragedy.”

The ceremony was a multi-denominational service with Teddy’s godfather, Akiva Goldsman, as the officiant. “We were lucky the weather gods acted in our favor,” Teddy jokes. “The Etsy witches Rose hired to cast a spell worked!” The groom walked up the winding path to Tank House hill along with the rest of the guests. “As the music changed, the moment we had been waiting for was upon us,” Teddy remembers. “Rose looked breathtaking. I come from a long line of men who cry, and I cried as I looked at the person with whom I will spend forever.”

“When I imagined my wedding day, it was always walking down the aisle that came to mind first,” Rose recalls. Standing behind Tank House, hidden from view, Rose and her parents waited for their cue. “We watched as my maternal and paternal grandparents began their procession down the aisle,” the bride says. “My parents both cried. There had been a time when it wasn’t guaranteed that all four of my grandparents would be there, let alone be well enough to walk on that day. Yet there they were—a living reminder of love, resilience, and family. It is a moment I will carry with me forever.”

Then it was their turn. “Every step felt exactly as it should,” Rose says. “I kept my eyes on Teddy the entire time. In that moment, with the people I love most surrounding me and the man I was about to marry waiting at the end of the aisle, everything felt perfectly, beautifully right.” The bride walked down the aisle arm in arm with both of her parents, and in a funny moment, accidentally kissed Teddy upon arriving at the altar, which was a simple glass podium with nothing but rolling hills of winter wheat behind the wedding party.

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