“We don’t care what these cars are worth. We care about the stories behind the cars. To be in the car world you must be into history. History is what’s important to me,” Gordon McCall tells me as we chat at The Quail, A Motorsports Gathering in Carmel, California.

Gordon is wearing a crisp white hat with the Quail Lodge & Golf Club logo, a navy blazer, a red and white checked shirt, white pants, and a pair of dark aviator sunglasses. His three-ring binder has fluorescent Post-it Notes sticking out from every corner, and even though we’ve just met, I take him for an accountant type and ask him some brainy over-considered question about the intersection of curatorial design and car collecting.

Gordon pauses, glances at the beautiful 2.6-liter V-8 1972 Alfa Romeo Montreal in Arancia orange we’re standing next to, and replies casually. “We’re not curing cancer here. This is about having fun.”

I think I have Gordon wrong. As business-focused as aspects of Monterey Car Week can be, Gordon founded The Quail to be a car event like no other—a celebration of all things motoring styled as a “garden-party extravaganza.” Its flawless organization and impeccable curation has carved a wide moat in an otherwise crowded car show schedule. “In 18 years this shit hasn’t been knocked off,” he says.

The Quail, with its coveted tickets, is decidedly not crowded, allowing for plenty of interesting car culture moments. I stumble upon Magnus Walker, the eccentric fashion designer turned car collector, eyeing the just-revealed Lamborghini Countach LPI 800-4. Does he like it? “Too soon to say,” Magnus tells me. I meet British racing driver and Formula One champ Jenson Button. Technically Jenson is there to promote the return of Radford Motors, a ’60s coachbuilder reimagined for the current market, but he can’t help but spend most of our chat showing off one of his most prized possessions—a rose gold Rolex Daytona he inherited it from his late father.

I take a glance at a limited-edition 5-liter V-8 Lexus IS 500 F in glossy gray Incognito when I meet another driving champ, Scott Pruett. Scott is also wearing a Rolex Daytona and jokes he got his “the easy way”—by winning the Rolex 24 at Daytona endurance race, something he’s done five times. He could have also said “the only way” as Rolex makes them strictly for Daytona champs. The day concludes with awarding a stunning 1938 Mercedes-Benz 540k Special Roadster the 2021 Rolex Best of Show. The immaculately persevered art deco beauty is one of only 25 and went through an eight-year restoration. Its owner was gifted a Rolex Oyster Perpetual Datejust 41.

post-war sports cars at the quail

Post-war sports cars (1961-1975) at The Quail, A Motorsports Gathering, 2021. Photo by Chris Force

The Quail is one of the many events during the annual Monterey Car Week. My next stop is the Rolex Monterey Motorsports Reunion, a validation of what fast cars are truly meant to do—go fast. Held at the iconic Weathertech Raceway Laguna Seca, nearly 400 period-accurate, museum-quality race and sports cars take to the track. The cars range from a 1949 Jaguar Parkinson Special to all types of Corvettes, Cobras, and Cooper Monacos. It’s nothing short of thrilling to see these types of cars barreling down the infamous Corkscrew—a blind turn that suddenly drops 5.5 stories in only 450 feet of track length. It’s hot, loud, smoky fun.

My last stop for the week is at the prestigious Pebble Beach Concours d’Elegance presented by Rolex. It’s considered the finale of Monterey Car Week and arguably one of the most coveted and glamourous vintage car shows in the world. Each of the 230 rare cars on display must be able to power itself to the 18th green of the Pebble Beach golf links, making the early morning arrival of the cars, referred to as “dawn patrol,” an event onto itself.

I watch as the cars, some of them millions of dollars and others priceless, some purring, some smoking, drive onto the green—temporarily creating the best moving museum on the planet. It’s part exhibition of design, part global history, and all celebration.

There’s a special exhibit this year, too: 38 previous Pebble Beach winners have been reunited for the show. Each winning car is mesmerizing in its own way, but I’m drawn to a group of early electric vehicles, including Richard Riker’s 1896 Riker Electric Prototype, a car his grandfather built in Brooklyn nearly 125 years ago. I watch as Richard drives the car onto the green with a grin on his face, his pin-striped three-piece suit and bow tie topped with a bowler hat. I imagine it’s something his grandfather might have worn.

I turn my attention to a car I think could be a show winner: a wild looking Mercedes-Benz I later learn is a 1937 540k Special Roadster. It’s stunning, with a villainous edge—I imagine Scrooge McDuck behind the wheel, complete with top hat, monocle, and cane. My prediction for winning car was close; that honor went to a 1938 540k Autobahn Kurier Mercedes-Benz. I watch as it drives up the winners stand, yellow and white paper confetti falling gently on its long sweeping hood. As the driver’s side door slowly opens I imagine a cartoon duck exit. Instead I see owners Arturo and Deborah Keller beaming from their win. “This is an incredibly special car that we really love, and it is very satisfying to win this prize and receive a Rolex.”

A version of this article originally appeared in Sixtysix Issue 07 with the headline “Monterey Car Week.” Subscribe today.

rolex.com/world-of-rolex

Read the best design stories from around the globe, each week.