One of my favorite places in the world is the Monterey Bay area along the central coast of California. I’ve regularly traveled to Monterey and adjacent cities such as Carmel-by-the-Sea and Pebble Beach since I was a child – perpetually enjoying the natural beauty and particular events found in the region. Each August, “Classic Car Week” fills the streets, hotels, and almost every venue, with people coming to town for the Concours d’Elegance, as well as related events which are all about celebrating (as well as buying and selling) beautiful and distinguished automobiles. For quite some time now, the official sponsor of the Concours and other events, such as that at the Mazda Speedway at Laguna Seca and the Quail Lodge show is Rolex watches. In this article, I’d like to explain what some of these events are about, share some experience of what it is like to be there, and attempt to persuade car lovers of all types to visit at least once in their life.

While the Monterey Classic Car Week is nothing new to me, experiencing it through the eyes of Rolex offers a fresh perspective on this important annual luxury lifestyle event. After the August 2014 Monterey Classic Car Week, I covered what it was like to spend time with and talk cars with long-time Rolex brand ambassador and race legend Jackie Stewart (if you are a car or racing person, I recommend you check that out). If you go, you may not get all the behind the scene’s access, but you’ll see the Rolex name around plenty. Rolex is keenly skilled in interacting with important demographics who not only have wealth, but also enjoy spending it on their passions and hobbies. Purchasing and maintaining classic cars is a serious labor of love which requires a lot more than just the money to do so. With that said, Pebble Beach isn’t just about buying and selling automobiles, it is also a celebration of something which is deeply connected to what we love about high-end objects – aesthetic elegance.

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Elegance is a fascinating concept to me, as it is so deeply ingrained in not only the high-end watch world, but the luxury world overall. Elegance is what keeps people interested in so many of these old cars. The funny thing is that people love the history, design, and stories of famous classic cars, but many are actually quite terrible to drive. None of that seems to matter much because the world’s fascination with automobiles combines an appreciation for art, engineering, and freedom as concepts. For many people, getting a car was their ticket to freedom when they were young, and having a cool car was their ticket to more social freedom and to a large degree was connected to more financial freedom. Driving a car can feel freeing, and owning the right car frees you to be yourself on the road. These are all powerful emotions, and present at all levels of car appreciation. But here in the Monterey area in August each year, you can experience an apex of automotive mania in quality and price.

Like its other “passion-driven” sponsorships and partnerships, Rolex was smart to work closely first with the Pebble Beach Concours d’Elegance and later other nearby events such as The Motorsports Gathering at The Quail, and the Rolex Monterey Motorsports Reunion races at Laguna Seca. While Monterey Classic Car Week slants toward vintage, it is by no means a place for only old cars and other vehicles. The world’s top car makers such as Ferrari, Lamborghini, Rolls Royce, Bentley, Aston Martin, and many more have an official presence at Pebble Beach. Whereas in the past, new cars debuted almost exclusively at auto shows for new cars, Pebble Beach in August is where many new high-end cars first make an appearance.

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Monterey Classic Car Week can be overwhelming to take in, even for veterans of what the events have to offer. Aside from some of the interesting auction events (if you are into that), Rolex more or less has a connection to each of the three major zones. The most important of which is still perhaps the Pebble Beach Concours d’Elegance. Rolex began to work with the Concours in 1997 as their “official timepiece.” Part of this honor allowed for a Rolex watch to be the prize of the show for the year’s winning car owner. The Concours d’Elegance is actually a competition with cars showing on the 18th hole on the greens of the famous golf course. Cars of all types and ages park in clusters according to their style and time of production. There are a series of ribbons given out but only one is the ultimate winner. For years now, comedian, television personality, and major car guy Jay Leno has be the award presenter.

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In addition to a ribbon, the winner with “the most elegant car” gets a Rolex watch with a special engraving on the back. This is actually a big deal and relates to something that other brands have tried to replicate, but really haven’t succeeding in doing. When someone wins a Rolex watch, they feel extremely special. It doesn’t matter if they can afford it or not. How is it that Rolex has succeeded in making it such a big deal to “win” a Rolex watch when so many of the people competing – no matter the sport or event – can in all likelihood just purchase the watch?

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The allure of a “won Rolex” is present around the world and is just as appealing if you are racing boats or an internationally known athlete – which, if you think about it, is pretty amazing. I think it has to do with part of what Rolex represents – an item marking success and accomplishment. Yes, in addition to Rolex making bar-setting watches for quality and value they have also worked hard to maintain an image as the “I made it watch.” You can’t deny the sales numbers even if you don’t personally want a Rolex watch. Rolex was also ranked the most reputable consumer product company in the world, according to one study earlier in 2014. So what I am saying is that a combination of actual high-quality as well as notoriety and desirability has made it so that even the richest of the richest sometimes compete extra hard just to get something as a prize that they could otherwise just buy. For them, it is about being competitive.

The competitive spirit is really what Rolex likes to attach itself to, even though it doesn’t outright say it. Car racing, classic car shows, tennis, golf, etc… these are all at their heart highly competitive events where there are losers, but also winners. And winners like to receive prizes for their efforts, don’t they? What better prize than a Rolex? At least, that is the idea Rolex has been successfully perpetuating for decades – and it just simply works without controversy.

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Sir Jackie Stewart with Sir Michael Kadoorie

What Rolex has been able to do is make everyone out there who wears one feel like part of that winners club. I’ve interviewed a lot of Rolex retailers over the years asking “what do customers talk about when shopping for a Rolex?” The responses aren’t all that different. New job, raise, bonus, anniversary, graduation… achievement, achievement, achievement… It is a trend I see time and time again. Even as some steeped in the nitty-gritty of the watch industry, I am not immune. When I got a Rolex for myself, it was to celebrate something.

With that said, we can return to sunny summer days on golf courses examining priceless automobiles and their owners. I last mentioned how the winner of the Pebble Beach Concours d’Elegance receives a Rolex watch. Rolex went from being just the official timepiece of the Concours d’Elegance to the title sponsor in 2007. In the immediate area surrounding the Concours is perhaps the most dense concentration of automotive activity. You can see a lot of new cars and concept cars on the golf course which are open to the public. Events like the Concours d’Elegance and The Quail require paid entrance fees.

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It was around 2001 that Rolex branched out to also participate in classic car racing as well as showing. Nearby to Pebble Beach is Laguna Seca (Mazda Raceway at Laguna Seca). The famous racing venue turns into a playground for owners of classic sports cars who spend days on the track doing what probably shouldn’t be done to many of the historic vehicles. Onlookers can see 1930s era race cars to modern exotic sport cars competing on the track. In all honesty, few of the drivers appear to be doing it to ultimately win. When you are cruising in an open top 1940s racecar as the owner, you are pretty much just happy wearing a helmet, goggles, and enjoying the opportunity to drive on Laguna Seca. Then again, some of the owners have been waiting all year to show off their drifting skills.

Rolex went from sponsoring the “Rolex Monterey Historic Automobile Races” from 2001 to 2009 to creating the more official Rolex Monterey Motorsports Reunion series that, for 2014, included 15 race groups comprising 550 pre- and post-WWII cars. You can’t help but constantly smile seeing the cars as well as the drivers having fun. This is perhaps the dirtiest some of these car owners get all year, with the dust blowing in their face. The Rolex name is everywhere on the track… and, of course, the winner also gets a Rolex watch.

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The newest addition to Rolex’s participation in the Monterey Classic Car Week is their sponsorship of “The Quail, A Motorsports Gathering,” which, I believe, they have been doing since 2011. The Quail is now owned by Sir Michael Kadoorie – owner of The Peninsula group of hotels – and a Rolex brand friend. The event at The Quail is also something not to miss and combines elements of the Pebble Beach Concours d’Elegance’s focus on classic cars with also new exotic cars and a lifestyle element.

Visitors to The Quail during “A Motorsports Gathering” pay to enter, but once inside, are treated with a rather special experience that includes complimentary food and drinks from local restaurants who set up areas around the periphery of the golf course where the cars are laid out for display. The unique blend of special vendors, new car brands, automobile customizers, and countless amazing classic cars makes for a very exclusive and fun atmosphere. Most people can easily spend a day or more at The Quail during Monterey Classic Car Week, and I’ve been fortunate enough to see this event continue to get better and better over the years.

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A Motorsports Gathering also includes a contest for best car, but rather than having third-party judges, the “Rolex Best of Show” car is actually selected by the owners after a number of cars are chose to be in the “Rolex Circle Of Champions.” If it all sounds “very Rolex,” it is, and the position of the major luxury brand in the event at The Quail most certainly makes them the envy of many other watch makers.

Is Rolex there in name only, or is their status as an important part of Monterey Classic Car Week represented on the wrists of car owners and tourists? That of course is the million dollar question for any company who invests in sponsoring a type of event for many years. You won’t find a lack of Rolex watches on people in all parts of the Monterey Classic Car Week. Then again, it is a great place for watch spotting of all types. Though yeah, if you are anywhere where cool cars might be Carmel-by-the-Sea, Pebble Beach, or Monterey during Classic Car Week, you’ll see a very healthy assortment of Rolex watches. It makes me wonder what it would be like for Rolex to make a car. The Swiss have done it before…

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