The first 'Del Monte Trophy' race was held on November 5th of 1950 on narrow town roads near the Lodge at Pebble Beach, originally traversing both paved two-lane roads and sections of dirt or loose gravel. The route began along Portola Road near the present-day equestrian center then followed the tight and twisty roads lined with tall Cypress trees along 17 Mile Drive. The starting grid was comprised of Allards, Jaguars, and MGs at first and, later, Porsches, Ferraris, and various racing 'specials.'

The Pebble Beach Road Races were held in tandem with the new Pebble Beach Concours d'Elegance, and admission was $1 which included free parking. Approximately 7,000 spectators watched from a hay bale-lined course as Phil Hill drove a Jaguar XK120 to victory.

2021 was the 70th Anniversary of the first Pebble Beach Road Race and in celebration, the Pebble Beach Concours d'Elegance showcased the vehicles that won the Road Races from 1950 through 1956, the final year for the race. Driver Ernie McAfee fatally slammed his Ferrari into a tree during the 1956 race, bringing the end to the popular Pebble Beach Road Races, and the genesis of Laguna Seca Raceway.

1950 Jaguar XK120 Roadster

This is the winning car from the very first Pebble Beach Road Races. In a dramatic and decisive victory, Phil Hill started at the back of the race because he had a shattered clutch, and as the race wore on he wore through most of his brakes, but he won by a substantial margin. The car itself (#670138) was Phil's own. After undergoing a brief period of service training with Jaguar, Phil purchased this early XK120 - one of just 240 aluminum alloy cars - and shipped it from Coventry to New York as his personal baggage on the Queen Mary. Modifications over the summer included boring the engine to almost 3.8 liters and stripping out needless weight - not just seats, bumpers, and windscreen but much of the underlying rear bodywork. Hill's historic racer eventually disappeared from the public's eye, but in the mid-1990s it was rediscovered in Marin County, having been under the same owner's care for the previous 36 years.

1951 Allard J2 Roadster

In the capable hands of Bill Pollack, this Allard J2 Roadster (#1850) won twice at Pebble Beach, in 1951 and 1952. On both of these occasions, Bill was driving for Tom Carstens, who had a team of mechanics, outfitted in matching overalls, to maintain the car. Presentation mattered to Carstens in 1952, and despite the weight considerations normal to racing, the car was outfitted with a luggage rack and whitewalls. With the car's Cadillac engine, power was not in question, and when Bill hit the gas pedal, acceleration was immediate. Bill recalled nearly driving off a steep road overlooking the Pacific when first testing the car the day prior to the 1951 race, and he also recalled with more than a bit of delight that his fast acceleration off the starting line on one occasion took out his primary competition, kicking up chunks of asphalt at another Allard. In addition to its success at Pebble Beach, the Allard accumulated a stellar record throughout both the 1951 and 1952 seasons; in fact, its first win at Pebble Beach marked the start of a string of eight consecutive victories.

1953 Ferrari 250 MM Vignale Spyder

This Ferrari 250 MM (0260 MM) took victory overall in the fourth Pebble Beach Road Races, held in 1953. This 250 MM is one of just two Series One Spyders produced by Vignale and the only one surviving with its original coachwork. It was delivered new by Ferrari racer and importer Luigi Chinetti to future Formula One champion Phil Hill, and Hill immediately entered the car in the 1953 Pebble Beach Road Races, finishing first overall. Hill continued to compete with the car, achieving several additional victories throughout that season. In addition to its racing pedigree, the car has done well at several concours events, placing first in class at the Pebble Beach Concours in 1990, and at the FCA Concours, and at Cavallino. The car was recently restored to its original specification, based on new research discoveries.

1953 Ferrari 340 MM Vignale Spyder

Ferrari 340s dominated the racing world in 1953, winning the Mille Miglia, the Tour of Sicily, at Silverstone and at Nurburgring. Ferrari built just 10 examples of the 340 MM before it was replaced by the larger 4.5-liter 375 MM, and this particular 1953 Ferrari 340 MM is the last of the ten 340 MM cars and the fifth to be bodied by Carrozzeria Vignale. The car shared many features with the 1952 Ferrari 340 Mexico Vignale Spyder that finished 2nd to Phil Hill's Ferrari 250 MM in the 1953 Pebble Beach Road Races, including the egg-crate grille, the three portholes, and the triangular cutaway extractors in the rear fenders.

In 1954 Sterling Edwards purchased this car and entered the Pebble Beach Road Races with it. He had helped to found these races in 1950 but although he often did well there, he had not yet won overall. He spun the car early in the trophy race but was quickly able to climb back through the field, and by the 10th lap, he moved into 3rd position behind Bill Stoppe's Kurtis and Tom Bamford's Cadillac-powered Allard. The Kurtis gave up on lap 28, and Edwards went on to victory.

1955 Ferrari 750 Monza Scaglietti Spyder

This Ferrari 750 Monza (0510 M) was raced by three of America's greatest racing drivers and it won at Pebble Beach not once but twice. In its first race, in March 1955, Phil Hill and Carroll Shelby drove the car at the Sebring 12 Hours race and were declared the winners before having to concede victory on a technicality to Briggs Cunningham's D-Type Jaguar. In April, Phil Hill won the Pebble Beach Road Races with the car and he continued to race it for the rest of the year. The car changed drivers in 1956 when Carroll Shelby took it over, winning the Pebble Beach races again as well as other events in California. Then Jim Hall raced the car for the 1957 season and was just as successful as his predecessors. Hall owned the car until 2016 when its current owner acquired it and undertook a mechanical and cosmetic restoration.

Pebble Beach Road Races Winners at Pebble Beach

The Pebble Beach Concours d'Elegance brought together all five race-winning examples for their 2021 event. The cars sat shoulder-to-shoulder along the ocean, just behind another special display of previous Pebble Beach Concours 'Best of Show' winners. During the awards ceremony, all five vehicles were invited to cross the awards stage.