From Garden Ceremony to Drag Disco: A Bold Wedding Weekend at Troutbeck

There are weddings, and then there are full-blown weekends that feel like a personal love letter to the couple, their people, and everything they love. In this case, Christian and Richard’s celebration at Troutbeck in the Hudson Valley was a letter penned to perfection.

We started working together well before the wedding weekend itself, beginning with their Brooklyn engagement party at the Wythe Hotel. It was colorful, social, and full of energy—an early glimpse of what was to come. From the start, it was clear they weren’t interested in a traditional playbook. They wanted something joyful, stylish, and completely personal.

They split their time between Brooklyn and Woodstock, so once the engagement party wrapped, it made perfect sense to host the wedding upstate. They chose Troutbeck, a 250-acre estate in the Hudson Valley with lush gardens, restored historic buildings, and just enough space to welcome 240 guests from around the world while still keeping the feel intentional and close-knit.

Our main priority was infusing as many personal touches and cultural nods from Christian and Richard’s backgrounds into the weekend. Christian’s family has South American roots, while Richard’s family is from England so those played a significant role in helping us shape the weekend.

Guests kicked off the weekend with thoughtfully curated welcome bags filled with the couple’s favorite things — a small but meaningful gesture that instantly made everything feel personal. Later that evening, the welcome dinner embraced Peruvian flavors and textures, setting a vibrant tone that hinted at the weekend ahead.

The next day, the ceremony unfolded in Troutbeck’s garden, lush and romantic, layered with emotion. One of the couple’s friends led everyone in a singalong of Everywhere by Fleetwood Mac — a warm, joyful nod to British church weddings that made the moment feel even more connected. Dinner followed under a beautifully dressed tent that struck a balance between elegance and playfulness. Christian and Richard burst into the tent to JLo’s Let’s Get Loud, tambourines in hand and pure joy in motion making it less “grand entrance,” more “instant dance break.”

As the reception hit its stride and the dance floor started to fill, we handed out Hora Loca swag to guests which instantly turned the energy up, honoring the high-spirited traditions of South American celebrations. And just when guests thought they’d seen it all — the afterparty happened.

When the band wrapped, we revealed a fully transformed ballroom: LED-lit dance floor, silver-on-silver lounge seating, and a giant mirrored installation overhead. It was like walking into an underground nightclub. The entertainment cherry on top was when the drag queens showed up. Let’s just say… Beyoncé would have approved and no one left until the final beat dropped.

Like most weddings, there were a few curveballs. One of them? A shipping issue with the couple’s custom seating chart — a beautiful piece created by Jubilee Paper.

We tracked it obsessively. As the big day got closer, it became clear the original wouldn’t make it in time. So my co-planner Meryl and her team stepped in and recreated it from scratch. No stress, no panic, no one the wiser. They hand-delivered the recreation just in time, and the couple never had to think twice about it. That’s the kind of behind-the-scenes work you don’t always see, but it’s exactly why having the right team matters.

There were a lot of memorable moments, but two really stood out for us.

The first was during the ceremony, when the singalong kicked off and the guests all joined in. It was warm, inclusive, and perfectly captured who Christian and Richard are: people who make everyone feel like they belong.

The second came later, when we pulled back the curtain to reveal the afterparty space. To see the guests’ reactions of shock and awe felt like such a satisfying way to close out the night.

Here’s your permission slip: You don’t have to choose between a traditional wedding and something wildly original. You can have an elegant tented dinner and a silver-drenched drag party. You can pay reverence to your roots and still throw in a Fleetwood Mac singalong just because you love it.

Be bold. Be personal. Have fun.

And if you’re dreaming of a wedding weekend like this one — thoughtful, layered, and unforgettable — you’ll want a planner who can help bring it to life (and troubleshoot the seating chart, just in case).