Motor racing’s story began with the earliest automobiles. Back then, it was worlds apart from today’s polished sport. Cars were crude, gas-guzzling giants, low on power and prone to breaking down. They lacked basics like windshields or proper cockpits. The drivers? Fearless young adventurers, pushing machines to their absolute limits for glory. As motor racing grew, it saw incredible changes and new rules. Today, governing bodies oversee every race with strict regulations. Let’s dive into ten legendary races, listed chronologically, that mark key milestones in this amazing journey.
1. The Gordon Bennett Cup Races (1900-1905)
The first international race series was the brainchild of James Gordon Bennett Jr., the wealthy owner of the New York Herald. In 1899, he offered a trophy to the Automobile Club de France. It was to be raced for annually by car clubs from various European nations. A key rule was that every single part of a competing car, right down to the wheels, had to be made in its home country.
The inaugural race in 1900 stretched from Paris to Lyon. Frenchman Fernand Charron won, driving a Panhard-Levassor. Out of the six races held until 1905, four were city-to-city sprints. The 1903 and 1905 races introduced circuit racing, held in Athy, Ireland, and at France’s Circuit d’Auvergne. This marked the earliest organized circuit racing, which later evolved into Grand Prix events after 1905. France dominated the Gordon Bennett races, winning four of the six. A British Napier (1902) and a German Mercedes (1903) claimed the other two victories.
2. The Vanderbilt Cup (1904-1910, Revived Later)
While Europe buzzed with racing series improving car technology, American enthusiast William Kissam Vanderbilt Jr. wanted similar progress in his country. So, in 1904, he started the Vanderbilt Cup. It was an international race open to all countries. Despite political and legal hurdles, Vanderbilt persevered. His cup became the first major trophy in American auto racing history.
The races took place on Long Island, and the early events (1904-1910) were incredibly exciting for their time. The Vanderbilt Cup also saw the rise of pioneering race cars like the Locomobile and Lozier. The venue later moved from Long Island to Wisconsin (1912), Santa Monica, and San Francisco until 1916, when America’s entry into World War I halted it. It was revived in 1936 by Vanderbilt’s nephew, George Washington Vanderbilt III, for a 300-mile race at the new Roosevelt Raceway. However, lack of American competition and a dull format led to its end after just two years. The cup saw another revival from 1960 to 1968, eventually merging with the Bridgehampton Sports Car Races.
3. The Targa Florio (Founded 1906)
One of the oldest endurance road races, the Targa Florio, was launched in 1906 by Italian driver Vincenzi Florio. The race looped around a 72-kilometer circuit, the Circuito Piccolo delle Madonie, through the mountains near Sicily. The very first Targa Florio covered three laps on treacherous tracks with challenging mountain curves and unpredictable weather. Alessandro Cagno won that inaugural 1906 race.
By the mid-1920s, the Targa Florio was a premier European race, predating both the 24 Hours of Le Mans and the Mille Miglia. In 1955, it became part of the FIA World Sportscar Championship, boosting its success. It became a stage for global racing legends like Juan Manuel Fangio and Stirling Moss to compete against Italian heroes like Tazio Nuvolari and Alfieri Maserati. The race’s international era ended in 1973, won by a Porsche 911 prototype. It continued as a national event until 1977, when a tragic crash forced its stop. Porsche’s classic 911 convertible was named “Targa” due to the brand’s success in this event.
4. The Peking-Paris Race (1907)
The idea for this legendary vintage car race came from a challenge in the Paris newspaper, Le Matin: “What needs to be proved today is that as long as a man has a car, he can do anything and go anywhere…Is there anyone who will undertake to travel this summer from Peking to Paris by automobile?” This audacious race spanned fifteen thousand kilometers across two continents, a seemingly impossible feat when cars were still viewed skeptically.
Forty entries were received, but only five teams shipped their cars to Peking (now Beijing). These included a Dutch Spyker, a French Contal 3-wheeler, two French DeDions, and an Italian 120 hp Itala, driven by Prince Scipione Borghese. Each car carried a journalist. The remote, unmotorized parts of Asia presented immense challenges: cars fell through bridges, needed hauling with ropes, got stuck in quicksand, and sputtered on benzene for fuel. The Contal 3-wheeler quit in the Gobi desert, its crew luckily rescued. After months of heroic effort, Borghese’s Itala reached Paris, days ahead of the Spyker. This race proved cars were here to stay and became an enduring adventure, reenacted multiple times, including a centenary event with 126 classic cars.
5. The New York-Paris Race (1908)
If the Peking-Paris race confirmed the automobile’s future, the New York-Paris race aimed to silence all remaining doubters. On a cold February morning, six cars from four countries set off from Times Square for the first round-the-world auto contest. Conditions were tough with few paved roads, forcing drivers to straddle railway tracks for miles. The original route planned to go to Alaska, then ship cars across the Bering Strait. However, extreme cold in Alaska led to a reroute through Seattle, then across the Pacific to Yokohama, Japan.
Motoring was new in rural Japan, where cars were an alien sight. From Japan, the route went to Vladivostok, Siberia. Progress slowed dramatically, measured in feet per hour. Finally, after a grueling journey across three continents, the European roads were a welcome relief. The winning US Thomas-Flyer reached Paris on July 30th, four days behind the German Protos. However, the Germans received a 30-day penalty for not going to Alaska before crossing the Pacific. The winning driver, George Schuster, was inducted into the Automotive Hall of Fame in 2010.
6. The Indy 500 (Started 1911)
Known as “The Greatest Spectacle in Racing,” the Indy 500 began in 1911 and is still held annually, usually on the last weekend in May, at the Indianapolis Motor Speedway. This prestigious race sees some of the highest speeds in circuit racing, with cars exceeding 320 kilometers per hour. The “500” refers to the total race distance in miles – about 200 laps of the Speedway.
Ray Harroun won the first Indy 500 driving a Marmon Model-32 based Wasp. His win was controversial as he raced without a riding mechanic, who typically monitored oil pressure and warned of overtaking cars. The large prize money ($50,000 in 1912) attracted international teams, including European brands like Fiat and Peugeot. Over time, engine size limits were introduced, following European standards. After the World Wars, the Speedway was neglected. Local entrepreneur Tony Hulman revived the track and the Indy 500, ushering in a golden age of post-war American motor racing.
7. The 24 Hours of Le Mans (Started 1923)
The 24 Hours of Le Mans is the world’s oldest and most famous active endurance race. Initially, it tested the reliability of production cars at the Sarthe Circuit in Le Mans, France. Over the years, it has attracted nearly every famous car brand and has been a hotbed for intense rivalries. The 1960s were particularly notable, with Henry Ford’s efforts to beat Ferrari leading to huge investments in race car development. Famous Le Mans racers include the Ford Mark IV, Ferrari 250 GTO, Porsche 917, and Chevrolet Corvette.
Le Mans introduced a unique starting procedure called the “Le Mans start.” Drivers would line up across from their cars, run to them at the flag drop, start the engines, reverse, and begin racing. This chaotic start became iconic but was later discontinued due to safety concerns about unfastened harnesses. Today, cars in the 24 Hours of Le Mans cover over 5,000 kilometers, roughly eighteen times the length of an average Formula 1 Grand Prix.
8. The Mille Miglia (1927-1957)
The Mille Miglia stands as perhaps the last of the truly legendary open-road races. Italian car enthusiast Count Aymo Maggi initiated it in 1927, even participating in the first event with his Isotta Fraschini 8A SS. The race started and finished in Brescia, covering a thousand unforgiving miles of Italian countryside. It showcased fine Italian grand turismo cars from brands like Maserati, Isotta, Fiat, Ferrari, and Alfa Romeo.
Despite its glamour and thrilling competition, the Mille Miglia was tragically cancelled in 1957. A devastating crash involving Ferrari driver Alfonso de Portago and his navigator, Edmund Nelson, also resulted in the deaths of nine spectators, five of whom were children. This accident marked a turning point for open-road racing, leading to increased safety concerns and the eventual end of many such events.
9. The Monaco Grand Prix (Started 1929)
The Monaco Grand Prix is arguably the most popular and prestigious event on the Formula 1 calendar. Along with the 24 Hours of Le Mans and the Indy 500, it forms the informal “Triple Crown of Motorsport.” The Circuit de Monaco, hosting the Grand Prix since 1929, is often described as an “exceptional location of glamour and prestige.”
Before 1929, Grand Prix circuits were typically in the countryside or on purpose-built tracks. The first Monaco Grand Prix brought racing to the city streets of Monte Carlo. Its tight, twisting, narrow course, which includes a famous tunnel, placed a premium on car maneuverability. Early editions were dominated by agile Bugattis, later giving way to the more powerful Alfa Romeo 8C Monza in the 1930s. Ayrton Senna holds the record for the most wins at Monaco, with six victories, including five consecutive wins from 1989 to 1993.
10. The Carrera Panamericana (1950-1954, Revived 1988)
The Carrera Panamericana was another historic road race, run on the roads of Mexico. It was originally started to advertise the newly completed Mexican section of the Pan-American Highway. The first race was a nine-stage, five-day event covering nearly 3,300 kilometers along the highway, from north to south Mexico. After just two years, it gained a reputation as one of the most dangerous races ever. This was due to its difficult course, sharp bends, and extreme changes in elevation – from 328 feet to 10,500 feet above sea level. Carburetors needed constant adjustment for the thinning air at higher altitudes.
Hershel McGriff and Ray Eliot won the first edition in an Oldsmobile. Other successful cars included the Mercedes-Benz “Gullwing” 300 SL and the Porsche 550 Spyder. Porsche enjoyed considerable success, winning many class-level victories, a testament to the reliability derived from the VW Beetle, an ancestor to many Porsche designs. Following a tragic crash at Le Mans in 1955, the Carrera Panamericana and similar road races were cancelled. However, it was revived in 1988 by Eduardo de León Camargo and continues to this day. Porsche named two of its car models, the Carrera and later the Panamera, after its team’s success in this race.
These ten races represent just a fraction of motor racing’s rich tapestry, but each played a crucial role. They pushed automotive technology forward, tested human endurance, and created legends that still echo in the roar of engines today. From treacherous city-to-city sprints to gruelling 24-hour marathons, these events laid the very foundation of modern motorsport.
Which of these historic races fascinates you the most? Did we miss any of your favorites? Leave your comment below and share your thoughts!
