The Rolex Winners of Monterey Car Week 2026

Winning Best of Show at one of Monterey Car Week’s prestigious events, such as The Quail or the Pebble Beach Concours d’Elegance, is the achievement of a lifetime – not least because the champion takes home a specially engraved Rolex watch. As a longtime partner of several of the week’s premier events, Rolex bestows these watches only on the owners of the very best cars.

Pebble Beach Best of Show: Rolex Perpetual 1908

The biggest prize this year went to Harry Yeaggy, whose ex-Clark Gable 1935 Duesenberg SSJ Special Speedster captured Best of Show at the 75th Pebble Beach Concours d’Elegance. Yeaggy received a specially engraved Rolex Perpetual 1908 watch, an appropriately traditional watch for what is unquestionably the most elegant automotive event in the world. Only two Duesenberg SSJ Speedsters were ever built, and Yeaggy’s example was originally delivered to Hollywood star Clark Gable.

The Quail Best of Show: Rolex Datejust 36

Yeaggy’s Pebble Beach victory added another distinction to one of the most celebrated American automobiles ever produced. Across the peninsula at The Quail, A Motorsports Gathering, one of the world’s top sports car collectors, Bruce Meyer, won the Rolex Best of Show award with his 1957 Ferrari 625/250 Testa Rossa. Meyer received a specially engraved Rolex Oyster Perpetual Datejust 36 and joined the event’s Rolex Circle of Champions.

Historic Racing Returns to Laguna Seca

But Pebble Beach and The Quail account for only part of Rolex’s presence during Car Week. At WeatherTech Raceway Laguna Seca, the Rolex Monterey Motorsports Reunion brought hundreds of historic competition cars back to the circuit for four days of racing, demonstrations and celebrations of motorsport history. Japanese motorsport took center stage in 2026, with Icons of Japanese Motorsport serving as the featured theme. More than 40 significant cars and motorcycles were assembled for the celebration, representing manufacturers including Mazda, Toyota, Nissan, Honda and Yamaha.

The Rolex Monterey Motorsports Reunion also brought together all six living American 500cc Grand Prix motorcycle world champions and welcomed back cars from the International Race of Champions. At the opposite end of the spectrum, more than 40 contemporary hypercars took to Laguna Seca for the inaugural Hypercar Parade, while Toyota used the weekend to give its new GR GT and GR GT3 their North American dynamic debuts.

The Spirit of Monterey and the Rolex Daytona

Rolex celebrated 25 years of association with the event this year, while the circuit’s prominent Rolex clock is modeled after a Cosmograph Daytona. The Reunion’s most coveted honor is the Spirit of Monterey Award, traditionally accompanied by a specially engraved Rolex Cosmograph Daytona. While the award was again presented in 2026, the recipient and watch have not yet been identified in the event’s official post-event recaps.

Three Rolex Watches for Three Distinct Events

With the Perpetual 1908 at Pebble Beach, the Datejust 36 at The Quail and the traditionally awarded Cosmograph Daytona at Laguna Seca, Rolex has created a trio of prizes that reflects the very different character of each event. The 1908 is a natural fit for the formality and prewar elegance of Pebble Beach, while the Daytona’s long association with motor racing makes it equally at home at Laguna Seca.