Rolex at Monterey Car Week 2026: When Winning a Concours Means Winning a Rolex

For one week every August, the Monterey Peninsula becomes the center of the collecting universe, and two worlds that share more than they admit stand in the same place. Car collectors and watch collectors are, more often than not, the same people, and no brand understands that overlap better than Rolex. Having supported the week’s gatherings since 1997, the crown was the connective thread across all four of its marquee events in 2026, timing the action from the paddock to the lawn. And at the biggest of them, it did something no other partner does: it sent the winners home wearing the prize.

Where the Best Cars Win a Rolex

The week’s pinnacle, the Pebble Beach Concours d’Elegance, marked its 75th edition on August 16, with Ferrari as featured marque and a tribute to the legacy of the 24 Hours of Le Mans. When a 1935 Duesenberg SSJ Special Speedster took Best of Show on the 18th fairway, its owner, Harry Yeaggy, was presented with a specially engraved Rolex Perpetual 1908, the brand’s most classical dress watch, to mark the achievement. “Finally getting to the top again after 19 years is incredibly meaningful,” Yeaggy said. “I’m looking forward to trying on my beautiful new Rolex watch.”

It’s a fitting reward, because the two objects are judged the same way. A Best of Show car and a great vintage watch are both measured on originality, provenance, and the quality of their preservation, down to details most people will never see. That shared language is why Rolex belongs here. No brand sits more squarely at the intersection of horology and horsepower: the connection runs back to the 1930s, when Sir Malcolm Campbell set land-speed records on Daytona Beach with a Rolex Oyster on his wrist, and forward to the Cosmograph Daytona, still the definitive driver’s watch. The same collectors bidding on a Duesenberg are the ones chasing an early Daytona.

The Sound of History at Laguna Seca

The horsepower half of the week ran from August 12 to 15 at the Rolex Monterey Motorsports Reunion, where more than 400 of motorsport’s archival machines returned to WeatherTech Raceway Laguna Seca and its legendary Corkscrew, a blind entry followed by a five-and-a-half-storey drop. Rolex Testimonee Scott Pruett was among them, back behind the wheel of his 1991 IROC Dodge Daytona, and this year’s celebration honored Japanese motorsport, gathering competition cars from Honda and Acura, Mazda, Nissan, and Toyota. The event also marked the 25th anniversary of Rolex’s association with the Reunion, which it first partnered in 2001 before becoming Title Sponsor in 2010.

Elegance in the Valley

Between the two poles sat the week’s more refined gatherings. On August 14, The Quail, A Motorsports Gathering brought collectors to Carmel Valley for a garden party honoring the 100th anniversary of Route 66, complete with a dedicated run of Ferrari F40s and the largest assembly of Lamborghini Diablos yet seen. The Rolex Best of Show went to a silver 1957 Ferrari 625/250 Testa Rossa, whose owner, Bruce Meyer, received an engraved Oyster Perpetual Datejust 36 and a place in the Rolex Circle of Champions. A day earlier, the Pebble Beach Tour d’Elegance, presented by Rolex since 2007, sent 200 storied cars on a figure-eight route through the Del Monte Forest and past Cypress Point, a rolling preview of the Concours and a nod to the original Pebble Beach Road Races of the 1950s.

A Century in Motor Sport

All of it rests on a relationship nearly a hundred years deep. Rolex’s family of motorsport Testimonees began with Sir Jackie Stewart in 1968 and now includes Tom Kristensen, the record nine-time winner of Le Mans, Mark Webber, Jamie Chadwick, and Nyck de Vries, who won the 24 Hours of Le Mans this year. The brand times the Triple Crown of Endurance Racing, the Rolex 24 At Daytona, the Twelve Hours of Sebring, and Le Mans, and lends its name to classic gatherings from Pebble Beach to the Goodwood Revival. As Kristensen put it in Monterey, “What unites them is the commitment of the owners who aspire to restore or maintain their car’s immaculate condition. Rolex aligns with these classic automotive events and the excellence on display.”

For the car-watch enthusiast, that is the whole appeal. Monterey Car Week is less an event than an annual pilgrimage, the one place where the two great mechanical passions are treated as one, and where the finest machines are honored with the finest watches. On the evidence of 2026, that union has never looked stronger.

Adrienne Faurote

Editor in Chief · Haute Time

As a former New Yorker, now a “Miamian,” Adrienne Faurote joined Haute Living in August of 2021. She currently serves as the Haute Media Group Editor-in-Chief, overseeing all editorial platforms within the Haute Media Group while also maintaining her role as Fashion, Jewelry & Watch Director. Prior to her position at Haute Living, Faurote was the Market Editor at Marie Claire Magazine US, amassing over ten years in the industry, becoming an authoritative voice in all things fashion, jewelry, and watches.