Distinguished Gentleman’s ride North Fork 2026

Jun 11

Distinguished Gentleman’s Ride North Fork 2026 was a challenge from the very beginning. Yet somehow, what started with uncertainty, stress, and a lot of winter planning ultimately became our biggest and most memorable year yet.

After previous years at Breeze Hill, Clay and I knew we needed to find a new home for the ride — somewhere reliable, welcoming, and financially realistic for a grassroots fundraising event. Throughout the winter, we spent countless weekends visiting beautiful properties across the North Fork, only to discover that many venue fees were simply beyond our reach.

As the clock was ticking, our friends Steven and Rachel Braverman introduced us to their neighbor, Giovanni Borghese, who graciously welcomed our riders to Borghese Vineyard for this year’s event. In what felt like perfect timing, that same day we also connected with Tuckers Taproom, who enthusiastically offered to host our post-ride gathering and lunch.

Suddenly, all the pieces started falling into place.

With the incredible support of Robin’s Nest Naturals, the event began to take shape. Christopher Robinson once again stepped up in a huge way — helping promote the ride throughout western Long Island while also organizing prizes for our top fundraiser, most dapper rider, and Best Bike in Show.

I was also thrilled to welcome back our talented photographer and videographer, whose work beautifully captures the spirit of this event year after year. Adding to the excitement, Hamptons Ink joined us with their tattoo truck, offering flash tattoos throughout the afternoon and bringing an entirely new energy to the celebration.

At times, fundraising felt slower than previous years, and a few of our major fundraisers were unable to attend. Naturally, that brought some disappointment. But as the ride drew closer, registrations surged, donations poured in, and the momentum became undeniable.

And then… it was finally ride day.

The weather could not have been more spectacular. Warm sunshine blanketed the North Fork as spring vines burst to life throughout wine country. Riders began arriving as early as 10am, gathering among the vineyard rows for coffee, bagels, conversation, and glasses of Borghese wine before the engines fired to life.

Before the ride began, one of the most meaningful moments of the day came when Pastor Jerry Halpin from North Shore Christian Church gathered our crowd together for a blessing over the event.

This was the first year we incorporated a formal prayer into the ride, and honestly, it became one of the moments that stayed with me most afterward.

Standing together among the motorcycles, vineyards, and riders from all over the world, it felt incredibly grounding to pause before the day began and simply express gratitude — gratitude for this community, for the opportunity to gather safely together, and for the men we were riding to support.

Pastor Jerry’s words reminded us that while this event is fun and celebratory, there is also something deeply meaningful at its core. Saying prayers together for a safe and successful ride brought a sense of peace and perspective to the morning that I’m truly thankful we included this year.

Another memorable highlights for me personally was welcoming the Nettesheim Museum crew. Peter Nettesheim brought several rare vintage motorcycles from his collection, while executives from BMW Germany traveled overseas to experience the event alongside us. Seeing those extraordinary motorcycles surrounded by dapper riders in such a beautiful setting perfectly embodied the spirit of the Distinguished Gentleman’s Ride.

Because at its core, this event is about far more than motorcycles.

It’s about community. Camaraderie. Brotherhood. It’s about showing up for the men in our lives — fathers, brothers, sons, husbands, and friends — and helping raise awareness and funding for men’s mental health and prostate cancer research. Without the health of the incredible men who make up this community, none of this exists. There is no ride without them.

And that’s what continues to make me so emotional and grateful every single year: seeing people come together not only from within the motorcycle world, but far beyond it, rallying behind this cause with generosity, compassion, and genuine kindness.

The ride itself was absolutely stunning.

Thanks to Giovanni Borghese’s generosity, riders departed directly through some of the oldest vines on the North Fork before winding their way toward the breathtaking roads surrounding Orient Beach State Park. It was one of those perfect North Fork spring days that reminds you just how lucky we are to call this place home.

Ending the ride at Tuckers Taproom could not have been more perfect. Riders relaxed indoors and out with incredible smoked barbecue, cold drinks, live music, and great conversation long into the afternoon. Musician SteveOffTheCouch — a rider himself — even donated his tip jar proceeds to the fundraiser, another example of the generosity that surrounded this entire day.

Clay and I also finally gave in and got matching DGR banner tattoos from Hamptons Ink — and we were blown away not only by Mike’s fine-line work, but by his warmth, professionalism, and true gentlemanly spirit. The same could be said for Chris and the entire team at Tuckers, who handled a crowd of more than 120 riders and guests with nonstop hospitality and positivity all afternoon.

I am incredibly proud to share that this amazing community has already raised nearly $40,000 for men’s health this year.

That number represents far more than dollars.

It represents conversations. Support. Awareness. Brotherhood. And proof that even in a small corner of the world like the North Fork, people can come together and make an incredible impact.

To every rider, donor, sponsor, volunteer, photographer, business owner, supporter, and friend who helped make this event possible — thank you from the bottom of my heart.

The gallery below reflects a handful of moments that were especially meaningful to me as host. They're the memories that immediately come to mind when I think back on this year's ride.

But this event was about so much more than any one person's perspective. Thanks to the incredible work of Corinne and Toan, the full story of the day has been preserved far better than I could ever tell it myself. Through photographs, interviews, and candid moments, they captured not only the motorcycles, but the people and purpose that bring us together each year.

I hope you'll take a moment to explore Corinne's full gallery and watch Toan's film using the links below.