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A British-American “Tailored, Masculine, and Moody” Autumn Wedding at Castle Hill Inn

By Sara Dial | Photography by 

Tim Willoughby 

|Planning by 

Hummingbird Events and Design

When Jake Kringdon-Dillon and Ryan Kringdon-Dillon shared a first date at Vin Sur Vingt, a wine bar in New York City, the pair sipped rosé, spoke for hours, and by the end of the night, knew they’d found something special. Three years later, the couple headed to Tiffany & Co. and purchased engagement rings—shortly thereafter, Ryan proposed. 

Jake had arranged for Ryan’s dad to call with news of a potential real estate client and that he planned a dinner meeting in the city. “Given that I was ushering us into the city at a very specific time, not to mention, I was suggesting outfits to wear—I think Jake knew it was happening,” Ryan remembers. 

“I definitely knew what was happening that day. Not only because Ryan was so desperately trying to keep me on schedule, but because my dad is a bad liar” Jake laughs. “I was excited but also a nervous wreck. I couldn’t believe the day was finally here.” 

When the two walked into Bryant Park, Ryan dropped to one knee in front of the fountain. In the time they spent sharing purposeful words, a crowd gathered and applauded as Jake said, “Yes.” “As a Brit, I felt like I was in a Hallmark movie. It was a very quintessentially New York City moment and definitely one that I’ll never forget. It was really special,” Jake says. Following the proposal, the couple’s families emerged from their hiding places and the group headed to Tavern On The Green. “The perfect ending to a beautiful day.”

Once engaged, the two agreed upon hosting their fall wedding somewhere coastal that was equidistant from Boston and New York. “We ultimately picked Newport and Castle Hill Inn for the historic New England charm and because we wanted a tented wedding and couldn’t resist the insane scenery and backdrop of the water,” Jake explains. “We went with what my mom ended up calling a ‘garden party chic’ aesthetic. It was tailored, masculine, and moody.” 

Jake’s mother, Jane Kringdom, was instrumental in the planning process, and Mandy Connor of Hummingbird Events and Design brought their vision to life, offering her professional expertise along the way. RSVP Hingham invitations set the tone for the weekend. 

On the day-of, Jake and Ryan donned matching custom tuxedos by Knot Standard. “We had many discussions about the specific shade of navy we would go with and after seeing a ton of swatches in person, we ultimately settled on a color called ‘midnight navy,’” Ryan shares. “We got to pick linings that reflected each of our personalities and added each other’s initials and the wedding date to the collars of our shirts and the inside of our jackets.”

On October 8, 2022, the grooms met before an archway of Stoneblossom florals and exchanged meaningful words before loved ones. “Looking out into a sea of friends and family in this beautiful setting just felt surreal,” Ryan says. “We felt so incredibly loved.” 

Once pronounced officially wed, the newlyweds shared a kiss and exited to Stevie Wonder’s “Signed, Sealed, Delivered.” All the while, guests waved American and British flags—a surprise courtesy of Jake’s mom. “We were already emotional, but we just lost it at this point,” Jake recalls. “We felt so much joy and happiness and the love we were surrounded by was palpable.”

Afterward, everyone traveled to a glowing reception space detailed with copper-colored glassware and lush florals. The Sugarbabies Inc. added to the ambiance of it all with beautiful music, as salmon and roasted squash made their way to each table. 

Jake and Ryan danced to James Vincent McMorrow’s “Higher Love,” before guests joined in on the celebrations. The two cut their Confectionery Designs wedding cake and spent a moment taking it all in. They jointly conclude, “Having all of these people from different points in our lives together in one place—we certainly felt the love.”