A Week of Rolex Watches at Monterey Car Week

A week full of Rolex watches at Pebble Beach.

Every August, Monterey Car Week transforms the California coastline into a playground for the world’s most passionate automotive and luxury lifestyle enthusiasts. From the roar of vintage race cars at the Rolex Monterey Motorsports Reunion to the elegance on display at the Pebble Beach Concours d’Elegance, the entire week pulses with exclusivity, heritage, and style. But beyond the rare sheet metal and million-dollar bidding wars, it’s also one of the best times of the year for watch-spotting.

Collectors and enthusiasts alike use the occasion to show off their most coveted timepieces—especially those from Rolex, a longtime sponsor of some of the week’s most prestigious events. Between the high-speed action and scenic coastal drives, it’s the perfect setting to let a well-chosen wristwatch shine. With that in mind, we at duPont REGISTRY are highlighting our favorite Rolex watches to wear while you’re on the peninsula, blending timeless horology with the unforgettable atmosphere of Monterey Car Week.

Rolex Monterey Motorsports Reunion

Rolex Daytona Cosmograph (Ref.126508)

Price: $48,400

A large group of vintage and modern race cars are lined up on a race track under a Continental Tire arch during Monterey Car Week, with tents and hills in the background.

A gold Rolex chronograph watch with a green dial and gold subdials, displayed on a gold metal bracelet—an exceptional choice for watches enthusiasts attending Monterey Car Week.

The Rolex Monterey Motorsports Reunion is a standout event during Monterey Car Week, bringing decades of racing history back to life at WeatherTech Raceway Laguna Seca. With its deep ties to motorsport, the Rolex Daytona feels right at home in this setting. Whether you’re watching the action unfold from the corkscrew or walking the paddock, the Daytona’s mix of timing function and racing roots makes it a fitting, low-key choice for a day at the track.

Pebble Beach Tour d’Elegance

Rolex Oyster Perpetual 36 (Ref.126000)

Price: $6,350

Classic cars drive past large crowds at the starting line of the Pebble Beach Tour d’Elegance, a highlight of Monterey Car Week, with banners, sponsor logos, and luxury watches on display overhead.

A silver Rolex Oyster Perpetual wristwatch with a beige dial, silver hour markers, and a metal link bracelet is shown against a white background—an elegant choice for watches enthusiasts attending Monterey Car Week.

The Pebble Beach Tour d’Elegance is all about enjoying vintage cars in motion, trading concours lawns for winding coastal roads. It’s a celebration of drivability—and that’s where the Rolex Oyster Perpetual shines. With its clean design, robust case construction, and versatile wearability, it’s a no-nonsense watch that doesn’t try too hard. Much like a well-sorted classic car, the Oyster Perpetual delivers quiet confidence, making it a fitting companion for a day behind the wheel.

Pebble Beach Concours d’Elegance

Rolex Day-Date 40 (Ref.228239)

Price: $47,500

A silver Rolex watch with a blue dial, displaying the day at 12 o'clock and date at 3, featuring a fluted bezel and metal bracelet—a timeless choice for watch enthusiasts during Monterey Car Week.

The Pebble Beach Concours d’Elegance brings together the world’s finest vintage and collector cars in a setting that leans more formal than most Car Week events. For an occasion like this, the Rolex Day-Date 40 makes a subtle statement. Its classic proportions and subtle yet refined presence fit right in among tailored outfits and polished chrome, offering a watch choice that’s understated yet appropriate for one of the week’s most prestigious gatherings.

This article appeared in our September 2025 Issue.
Introducing the August 2025 issue of duPont REGISTRY, #484, starring McLaren Automotive’s 2027 Le Mans Hypercar. To get your hands on a copy, either buy a single issue or subscribe.

Photos Courtesy of Pebble Beach Concours/Rolex