Ringside with Bobby Ginsberg: The Heart of Hamptons Equestrian Life

Few names in the Hamptons equestrian world carry the same weight as Bobby Ginsberg. A competitor, mentor, and tastemaker, Ginsberg’s influence stretches from the show ring to the real estate market—and even the roots of the Hamptons Classic itself. 

Before the Classic became the high-profile event it is today, it was first held at the Southampton Hunt & Riding Club, a storied property whose Clubhouse Bobby transformed into a refined estate now located at 2 Dovas Path. Carefully renovated to preserve its equestrian character, the home blends heritage with luxury in a way that only someone like Bobby could envision.

For Ginsberg, this year’s Hamptons Classic was a return to form and then some. Though he wasn’t in the ring himself, he had a front-row view of what he calls “the best Classic in recent memory.” I caught up with him to talk about the event’s evolution, the future of equestrian sport on the East End, his new barn in Wellington—and the one property that captures the soul of Hamptons equestrian life.

What stood out to you about this year’s Hamptons Classic?

This year had a really fresh energy. It just felt like more people attending and seating around the rings – an excitement and energy you could feel. People were showing up and staying. Every time I walked through the boutique garden, it was packed. There was a real buzz.

Any improvements behind the scenes that made a difference?

The organization was impressive across the board. I have to shout out the parking situation—it was seamless, which anyone who’s ever been knows is no small feat. Even in the main tent on Sunday, I could actually see the jumps, which was a different experience for me since I wasn’t competing this year. It felt very people-friendly. Lots of coordination, lots of help. They nailed it.

You’ve seen a lot of horse shows over the years. What makes the Classic so special right now?

It’s one of the last great horse shows on Long Island. I used to run three shows leading up to the Classic—those have faded. But the Classic brings it all back. You’ve got international-level riders coming in—this year, a Brit won. For them, it’s not a hobby. It’s a profession. They’re here chasing serious prize money.

There’s been talk of more shows returning to the area. Is that real momentum or just talk?

There has been talk about Brianne Goutal and her husband (who own Two Tree Stables) bringing back three weekends of horse shows leading up to the Hamptons Classic. I used to run these shows for that exact reason – as a warmup for the Classic. That’s huge. It’s going to attract amazing talent and bring that equestrian energy back to the Hamptons.

How do you feel about the lifestyle side of the Classic—the events, the activations, the crowd?

The lifestyle piece has evolved in a really thoughtful way. These aren’t just branded pop-ups—it’s all done with a nod to the equestrian world. It feels organic. You’re not walking through some product maze. It’s built around the culture of riding, and it resonates.

Tell us about the equestrian history of 2 Dovas Path in Southampton.

2 Dovas Path sits on what was once the Southampton Hunt & Riding Club—so there’s a rich equestrian legacy built into the property. You can still feel that history when you walk the grounds. The estate originally had a half-circle driveway designed for horse-drawn carriages, which tells you how deeply tied it is to the riding culture out here. It’s rare to find a property that’s so connected to that world and still so close to Southampton Village and the ocean.

The renovations are impressive. What is the estate like now?

We really focused on honoring the property’s history while making it livable and luxurious for today. It’s not trying too hard—it’s not pretentious. There’s a warmth to it. I opened up the interiors with soaring ceilings and beams in the kitchen and great room. I refurbished some unique chandeliers with equestrian motifs—they’re like new and hang in the original location. I really put a lot of time, energy, and thought into the renovations.

It has this effortless flow between indoor and outdoor living—great room for entertaining, patios for gathering, and my favorite space: the screened-in middle room, which once hosted members at the Club. It really captures the home’s original character.

We also redesigned the entryway, replacing the old carriage loop with something more private and welcoming. 

What’s new in your world? You’ve spent a lot of time in Wellington lately.

After years in Southampton, I just opened a new farm—Southfield Farm—in Wellington. It’s the most beautiful barn I’ve ever been privileged to have horses at. It reminds me of the barn and stalls I had in Southampton – it has a real iconic feeling. I can’t wait to invite some old clients who rode with me to see the new barn and new beginnings in Wellington.

And you’re mentoring the next generation now, too?

That’s maybe the best part. I’ve always been a true competitor, but it’s rewarding to pass that knowledge on. We’re showing again, and we’re winning! It is so meaningful to be involved in equestrian life.  I’ve got some incredible younger riders I’m working with, and it feels like keeping a tradition alive. That kind of continuity matters to me.

To learn more about Bobby Ginsberg, click here.