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.
