Inside Monterey Car Week 2026: Rolex, Pebble Beach & the Greatest Cars in the World

Every August, the Monterey Peninsula becomes the most important address in the automotive world — and this year, the 75th edition of the Pebble Beach Concours d’Elegance made it more so than ever. From the thundering machines at WeatherTech Raceway Laguna Seca to the immaculate show cars lining the 18th fairway at Pebble Beach Golf Links, Monterey Car Week 2026 delivered four days of motoring at its finest — and at the center of all of it, as it has been since 1997, stood Rolex.

Photo Credit: ©Rolex/Tom O’Neal

The week’s four signature events — the Rolex Monterey Motorsports Reunion, the Pebble Beach Tour d’Elegance presented by Rolex, The Quail by The Peninsula, A Motorsports Gathering, and the Pebble Beach Concours d’Elegance — each carry a Rolex clock as their timekeeper, a symbol of the Swiss watchmaker’s nearly three-decade commitment to automotive excellence. Rolex Testimonee Tom Kristensen, the nine-time winner of the 24 Hours of Le Mans, put it simply: “Monterey Car Week is a tapestry of superior car events that are all so different but fit so well together. Rolex aligns with these classic automotive events and the excellence on display.”

Photo Credit: ©Rolex/Tom O’Neal

The week’s crowning moment came Sunday at the 75th Pebble Beach Concours d’Elegance, where a 1935 Duesenberg SSJ Special Speedster — owned by Harry Yeaggy — claimed Best of Show. Ferrari held the honor as featured marque during the anniversary celebration, reflecting its storied presence at the Concours since the early 1950s, alongside a tribute to the legacy of the 24 Hours of Le Mans. Yeaggy received a specially engraved Perpetual 1908 from Rolex. “This is the most special car event in the world,” he said. “I’ve come close several times, so finally getting to the top again after 19 years is incredibly meaningful.”

Photo Credit: ©Rolex/Tom O’Neal

Photo Credit: ©Rolex/Tom O’Neal

An essential prelude to the Concours, the Pebble Beach Tour d’Elegance presented by Rolex took place Thursday, August 13, with a 200-strong line-up of the world’s most storied automobiles navigating a picturesque figure-eight route through the Del Monte Forest, past Cypress Point and the prestigious Spyglass Hill Golf Course — a route that echoed the original Pebble Beach Road Races of the 1950s.

On Friday, August 14, The Quail by The Peninsula, A Motorsports Gathering drew the industry’s most prominent collectors and manufacturers to Carmel Valley for its signature garden party. This year’s edition honored the 100th anniversary of Route 66 with a winding display path replicating America’s legendary highway, alongside a dedicated collection of Ferrari F40s and the largest assembly of Lamborghini Diablos ever gathered. The Rolex Best of Show was awarded to a sleek silver 1957 Ferrari 625/250 Testarossa, owned by Bruce Meyer, who received an engraved Oyster Perpetual Datejust 36 and saw his car admitted to the Rolex Circle of Champions. “I am deeply touched to win a show like this,” he said. “Thank you to Rolex for this moment — I couldn’t be more thrilled.”

Photo Credit: ©Rolex/Tom O’Neal

Wednesday through Saturday, WeatherTech Raceway Laguna Seca came alive for the Rolex Monterey Motorsports Reunion, welcoming more than 400 of motor sport’s most important historic machines to the track. This year marked the 25th anniversary of Rolex’s association with the Reunion — having first partnered the event in 2001 before becoming Title Sponsor in 2010. Rolex Testimonee Scott Pruett returned to the track behind the wheel of his 1991 IROC Dodge Daytona, while a special celebration of Japanese motor sport put vehicles from Honda/Acura, Mazda, Nissan, and Toyota at center stage.

Photo Credit: ©Rolex/Tom O’Neal

Photo Credit: ©Rolex/Tom O’Neal

Rolex’s relationship with motor sport stretches back to the 1930s, when Sir Malcolm Campbell set World Land Speed Records on Daytona Beach with a Rolex Oyster on his wrist. Today, that commitment spans the FIA World Endurance Championship, the IMSA WeatherTech Sportscar Championship, the Rolex 24 At DAYTONA, the Twelve Hours of Sebring, and the 24 Hours of Le Mans — alongside Testimonees including Sir Jackie Stewart, Tom Kristensen, Mark Webber, Jamie Chadwick, and Nyck de Vries, who won the 24 Hours of Le Mans in 2026. At Monterey, as with everything Rolex touches, the standard is excellence — measured not in trophies alone, but in the extraordinary machines and the people devoted to preserving them.

For more of Haute Living’s luxury automotive coverage, read our Ferrari 12Cilindri review and the definitive luxury cars and supercars guide.