How Rolex Keeps the Magic of Monterey Car Week Alive in Changing Times

If San Diego Comic-Con is the mecca for pop culture fans, then Monterey Car Week is its four-wheeled equivalent—a weeklong celebration of the past, present, and future of motorsports and the automobile. Growing up in San Diego, I’ve seen firsthand how Comic-Con transforms the city. It’s not just the convention center—it’s the Gaslamp, the hotels, the pop-ups, the crowds spilling into every corner of downtown. Car Week feels the same way. It’s a full-on scene.

At the same time, there’s an undercurrent of tension surrounding it that keeps getting stronger. Influencer culture has blown up the spot, with larger crowds than ever, more unsanctioned events (including a takeover at a local In-n-Out this year), and a lot of people who seem more interested in going viral on TikTok than soaking it all in.

The thing that gets lost in this debate is that Monterey is still big enough—and traffic is bad enough—that in reality there are a thousand different Car Weeks depending on how you approach it. You can string together any number of free shows like the all-German Legends of the Autobahn or Woodies in the Woods, which is exactly what it sounds like; spend your entire time at Laguna Seca getting way too close to famous race cars; watch people blow millions on cars at the auctions; bump into CEOs like Jim Farley or Christian von Koenigsegg getting coffee; attend panels and film screenings hosted by cultural icons; or simply go car camping with other regular people.

But what about the “classic” Car Week experience: Friday at The Quail, Saturday at Laguna, and Sunday at the Pebble Beach Concours? To see if that trio still has the same draw amid all this change, I tagged along with Rolex, one of the week’s longtime big sponsors, and ran through the full gamut. And honestly, I came away convinced that there’s nowhere for a car person like Monterey in August, even if it is a little rowdier at the edges. The whole place buzzes with an energy you can’t fake or recreate.

Day 1: The Quail, A Motorsports Gathering

And why does Rolex do all this to support car culture and racing? Well, we wrote a whole story about that back in 2019; a lot has changed in the last six years, but thankfully Rolex’s backing of Car Week isn’t one of them. You might think a title sponsor is just a name on a banner, but no doubt the whole week would feel a lot different without the watchmaker’s connections, recognition, and exclusive draw amping up everything.

Friday kicked off with The Quail, A Motorsports Gathering, which Rolex has sponsored for 20 years now. Walking onto the grounds felt like being a kid stepping into Disneyland for the first time—except instead of costumes, Skechers, and mini portable fans, it was suits and ties, sunhats, and parasols. Cars you’ve only ever seen as digital renderings on Instagram were suddenly right there in front of you—at every corner, on perfectly manicured Bermuda grass. There are plenty of ways to describe the event’s meticulous curation, but to me, it’s the highest echelon of a car show—the red-carpet event of Monterey Car Week. Even the parking lot is a feast of car spotting.

Gordon McCall, the event’s Director of Motorsports, led me through the grounds, pointing out highlights like displays honoring the 60th anniversary of the Iso Grifo and the Shelby Mustang GT350. But honoring the past is only half the story at The Quail—the other half is celebrating what’s next. And nothing says “what’s next” quite like a car under a cover, waiting for its big reveal. There were plenty of those: Lexus’ hyped-up Sport Concept, the Gordon Murray S1 LM, and even restomod icons making an appearance. Singer, Guntherwerks, and even Ringbrothers—better known for SEMA—all brought the heat to the automotive garden party.

Two moments stood out: seeing 16 Ferrari F50s gathered on a golf course, and the growing JDM presence. Larry Chen’s R34 GT-R, multiple NSXs, an R33 400R, a heavily modified AE86, and my personal favorite, the Toyota 2000GT, all had spots on the lawn.

As if the cars weren’t enough, how about a chat with a nine-time Le Mans winner? Tom Kristensen turned out to be as down-to-earth as they come. He lit up when talking about his latest toy—not a race car, but the last Audi RS6 Performance.

“I’ve been through all these due to my job, but I’ve never owned one,” he said with a grin. “Now I bought myself one. I can put everything in the boot. I can put bikes wherever I go.”

Bikes? Turns out, post-full-time racing life means picking up gravel biking as a hobby. These days, it’s less about competition and more about the lifestyle.

“As I get older, I’m getting into gravel,” he explained. “Before it was all about having to be first. With gravel, I don’t care. You have coffee until four, after four you have beers. Then BBQ, preferably dining outside. It’s a lifestyle—slow down a bit, breathe. Look at the colors.”

Hearing him talk about trading checkered flags for sunsets and two wheels instead of four was unexpected, yet refreshing.

Sure, Tom is a Rolex brand ambassador, or testimonee as the company calls it, and Rolex hooked it up. But that (and the free food and drink) is why people pay $1500 for tickets—titans like him are everywhere in The Quail, wandering freely, available for casual conversations. The unguarded access to people usually protected by layers of handlers and PR reps is unparalleled. The Quail set the bar high, and the best was yet to come.

Day 2: Rolex Monterey Motorsports Reunion at Laguna Seca

If The Quail was champagne, Rolex Monterey Motorsports Reunion was an energy drink.

I had never been to WeatherTech Raceway Laguna Seca before, and rolling in, I could already hear the track was alive. The paddock was crammed with race cars spanning decades and disciplines—open-wheel legends, endurance prototypes, muscle cars, and more.

One highlight was the IROC cars, their liveries straight out of the 1980s, complete with carbureted V8s topped by big, round air cleaners. We even met Scott Pruett, a legend behind the wheel of many of those cars, who fittingly wears a Rolex with his winning races engraved into the back.

But the day’s showstopper for me was the Pagani Huayra R Evo running hot laps. The sound alone froze everyone in their tracks. Every pass down the straight was a neck breaker.

Then came my turn for a thrill: a hot lap in the new Mustang GTD during the lunch break. Strapped into the passenger seat, I felt like I was climbing onto a roller coaster, and with the iconic Corkscrew drop, it practically was one. The 5.2-liter supercharged V8 screamed to redline as the paddle shifts cracked like rifle fire. Its carbon-ceramic brakes, active aero, and Michelin Pilot Sport Cup 2s made handling the track a breeze. My driver talked through the entire spec sheet during the lap which was both hilarious and impressive given the speeds and g-forces we were hitting.

Even with what I assume was him driving at 70% effort, the Corkscrew was unreal. We dove 59 feet in a couple of heartbeats, carving through Laguna Seca’s most iconic corner. Pure exhilaration.

We ended the day at the top of the Corkscrew itself, watching classic racers tackle the turn from just a couple arm’s lengths away. But even though you need a hookup for that kind of special access, the beauty of Laguna’s hilly layout is that there are loads of spots to post up for a few hours and see literal history fly by.

Day 3: Pebble Beach Concours d’Elegance

Sunday was my first time doing Dawn Patrol—the tradition of watching the Pebble Beach Concours d’Elegance cars drive onto the famous 18th fairway before sunrise. It’s painful to get up before 5 a.m. after running nonstop for days, but so, so worth it.

By 6 a.m., I was on the grounds, camera in hand, watching priceless automobiles emerge from the mist. It was an incredibly serene experience. Imagine a picturesque cliffside Macbook screensaver, and then add hundreds of priceless cars into the frame that you’ll probably never see in motion again. I think that’s the real draw. Concours cars have to be in working order and drive themselves into the show to qualify.

Even if prewar cars aren’t your thing, the Concours is magical. The Quail highlights the cutting edge, Laguna Seca honors racing pedigree, but Pebble Beach showcases rolling works of art. Around 200 cars, each invited through an incredibly selective process, compete for Best of Show. They’re historical artifacts, preserved or restored to perfection and displayed against one of the most stunning backdrops on the West Coast. No matter your automotive niche, it’s impossible not to feel a deep appreciation for the vehicles on display. You could spend hours poring over the details of a single car, so I truly applaud the judges—my new friend Tom among them—for carefully evaluating every entry in just a few hours.

In the end, it was the 1924 Hispano-Suiza H6C ‘Tulipwood’ Torpedo that claimed Best of Show and took home the Rolex Perpetual 1908 awarded to each year’s winner. The car was a straight-up masterpiece. I mean, can you imagine? 12,000 man-hours dedicated to restoring a 100-year-old vehicle with a body made entirely of wood.

People will always complain about change, but the hits at Monterey Car Week still hit hard. The Quail, Laguna Seca, Pebble—they all deliver the same magic that’s made this week an epicenter for car culture for decades. Sure, the crowds are bigger, the influencers louder, and the edges a little rowdier, but that sophisticated, immersive charm remains at its core. Car Week is what you make of it, and if you’ve never been, start making plans for next August. There’s nothing else like it.