Monterey Car Week: A Photographer’s Journey Through the World’s Greatest Rolling Art Show

Every August, Monterey becomes the world’s biggest automotive art gallery. Roads clog with rolling sculptures, Ferraris, Lamborghinis, obscure one-offs, and forgotten treasures, transforming the peninsula into what I consider the best art show in the world.

My first voyage to Car Week in 2018 set the tone for everything that followed. I drove a Citroën DS21 Chapron all the way from Connecticut to California, a pilgrimage in its own right. On that trip, I made a friendship that still shapes my visits today. Each year since, I’ve had the privilege of staying with my friend John Mims who lets me borrow his 1992 Autozam AZ-1, the same quirky little kei car I now own back home.

This year, my calendar was packed before I even touched down. Fiat USA, DuPont Registry, and Concours d’Lemons were definite assignments, with Octane Magazine joining the list again for both Best in Show coverage and a feature piece. With so many clients, my schedule was airtight, leaving little room for the countless other events swirling around the peninsula.

I was also hired to cover the Hagerty Motorlux Hangar Party, which in my eyes sets the tone for the entire week. It’s the event that gets everything underway, blending elegant machinery with a lively atmosphere. I photographed everything from the rare cars on display to the joy of people reconnecting, laughing, and starting their Car Week adventures. It’s one of those gatherings where you can feel the excitement building, knowing the days ahead will only get wilder.

I also had the opportunity to photograph the Fiat Topolino at Laguna Seca as part of Fiat’s introduction of the model to the United States. We used the Topolino to move between different locations around the track while capturing its charm and character. It was a thrill to watch Ray Evernham dispatch the IROC class to the staging lane, highlighting the motorsport heritage that surrounds Monterey Car Week. Driving the electric Topolino was particularly memorable, with its responsive handling and the unique sensation of sitting further back in the chassis, giving me a full appreciation of its design and agility while navigating the track grounds.

By Thursday, sensory overload hit me hard. Monterey does that to you: too many cars, too much beauty, and too little time. I pressed pause with my friend Jim Dunaway of Bayberry Vintage Autos. We escaped to the aquarium and grabbed lunch, just to breathe. That evening, reality snapped back in at RM Sotheby’s Auction inside the Portola Hotel.

The first car I had photographed to cross the block was a 1971 Mercedes-Benz Pagoda, a special one for me because it was the first manual my wife had ever driven. She nailed it on her very first try, and all I needed was a rolling shot in a straight line. Fittingly, the car’s sale went 100% to charity. The following day, a Lamborghini Countach I shot took center stage, wearing the Boston cityscape I’d captured in the background like a tailored suit.

But this year felt different. I found myself pointing the camera at people more often than cars. Losing a few close friends recently has made me value the faces, the conversations, the moments between the machines. Hypercars, with their constant social media hype and endless iterations, seemed less magnetic. People, on the other hand, their passion, joy, and stories, pulled me in.

Jim and I also made time for something we’d both always wanted to do: the road tour to Bixby Bridge. We perched ourselves on a cliffside to get the shot, right next to Brian Kimball, one of Pebble Beach’s photographers. The twist? None of us are fans of heights. Balancing cameras on the edge of a cliff while trying not to look down made it one of the wildest and most memorable—moments of the week.

At Pebble Beach, I walked the field with Clint Sly, who kindly introduced me to many owners and their families, which led to some of my favorite portraits of the week. Photographing the ramp, however, remained a challenge, it’s been blocked for years, with security urging you along if you linger too long. I resorted to “drive-by shooting,” looping back and forth to get the angle I wanted. Personally, I prefer the backdrop of the crowd to the Lodge itself, it feels alive.

The day was long, hot, and relentless. Almost every time I walked back through the staging lanes, I’d spot another friend winning an award. That meant turning right around and running back to my shooting spot to capture their moment. By the time Best in Show was crowned, I was baked by the sun, exhausted, but grateful. I sat in the field until nearly 7 p.m., too drained to walk the half mile back, eventually caving and asking for a ride.

Once again, I had the honor of serving as the official photographer for Concours d’Lemons Monterey 2025. The event is best understood as a spoof, an irreverent counterpoint to the elegance of Pebble Beach, and its charm lies in originality. Too often, people assume they just need to bring something old or rough around the edges to fit the theme. In reality, it’s about creativity, humor, and commitment to a bit of theater. Costumes, themes, and tongue-in-cheek bribes for the judges (bacon still reigns supreme) are what define the winners. That’s why seeing something like an R32 Skyline show up misses the point entirely, because a true lemons car is about character, not collectability.

My week ended on a lighter note with Parker and Sheri Roaf of Parker’s Packards. We spent the final day together strolling through antique shops, revisiting the aquarium, indulging in ice cream, and laughing endlessly. Strangely, the streets were bare, no exotics, no classics, just work trucks and daily drivers. It was as if Car Week had been a dream that evaporated overnight.

That’s the magic of Monterey. For one week, the world descends on a sleepy stretch of California coastline, and the impossible becomes ordinary. And just as quickly, it’s gone, leaving behind memories, friendships, and photographs that remind you it really did happen.

👉 Photo link below to purchase images or prints.