The Spirit of the Hill | 2026 Wilbraham Hill Climb
There is something special about the Wilbraham Hill Climb that feels frozen in time. Dating back to 1908, the event is one of the oldest automotive hill climbs in the United States and continues to carry the spirit of early motorsport into the modern day. The narrow roads, the sound of engines echoing through the trees, and the small-town atmosphere make it feel less like a polished production and more like a gathering of people who genuinely love cars and the stories attached to them.
When I first arrived in the pits that morning, I came across Kobus Reyneke and a group of friends unloading their hand-built cycle karts from trailers. Each one was inspired by legendary race cars and crafted with so much personality that you could not help but smile walking past them. Before the racing even began, there was already a story unfolding. Watching them work together, joke around, and simply enjoy the morning reminded me why I love photographing these events in the first place.
This year, Ben Bragg took the win with an impressive time of 56.19 seconds, charging up the hill with incredible precision and commitment. But while the competition itself is exciting, I found myself drawn more toward the moments happening around the racing.
At one point during the day, I finally met Rick Lees from Enfield Auto Restorations in person. Rick has followed my photography career for quite some time, and during our conversation I found myself explaining something I do not think many people realize about event photography. It can actually be difficult to stay fully invested in a conversation because my mind is constantly scanning. I am always looking around for the next unexpected moment about to happen. A reaction. A gesture. A child pointing at a passing car. Someone laughing in the background. Those are the moments that disappear in seconds.
This time around, I intentionally focused less on just photographing cars racing up the hill and more on capturing the “fluff” of the event. The details that make the 2026 Wilbraham Hill Climb its own unique story instead of simply another hill climb. We had talented photographers on the team focused on the racing action itself, but I wanted to document the human side of the day. The placement of people around cars. The interactions. The atmosphere. The things that transport you back to that exact moment years from now.
Wayne Carini was there with his grandson Connor, which always makes me smile to see. Whenever I bring diecast cars with me while photographing vehicles for sale, Wayne usually hands them off to Connor. It is such a simple thing, but moments like that stick with you because they show how these events bridge generations.
Earlier in the morning, all the vendors had their booths set up and ready despite the cold rain. I walked around with probably a little too much enthusiasm for that hour of the morning, convincing vendors to step out front for photos with big smiles. Hopefully they can use the images someday for promotion, or maybe just as a memory from another rainy New England event that somehow still turned into a great day.
As the racers continued blasting up the hill, I wandered farther along the course and noticed a beautiful colonial home with a bright blue door sitting behind a stretch of vivid green grass. Something about the scene immediately caught my eye. The composition felt perfect before I even raised the camera, and thankfully it delivered exactly the way I imagined. Sometimes those quiet moments away from the loudest parts of the event end up becoming your favorite images of the day.
Later on, I noticed the oil dripping from old race cars mixing with the rainwater on the pavement. The colors shimmered across the road in a way that instantly reminded me of Rainbow Road from Mario Kart 64. It was one of those random little observations that probably only makes sense to someone wandering around in the rain for hours with a camera, but it became one of my favorite memories from the event.
At the end of the day, the 2026 Wilbraham Hill Climb felt like another one for the books.
A huge amount of credit goes to the Demarey family for hosting and continuing to preserve what makes this event so special. Beyond the racing itself, events like this bring people into the town of Wilbraham, support local businesses, and create memories that stick with people long after the engines go quiet.
That is what keeps everyone coming back year after year. Not just the cars, but the feeling.