Buzz
The origins of motor racing go back to the very birth of the automobile. Back then, racing was quite different from what we know today. The cars were massive, inefficient machines with little power and prone to breaking down. They didn’t have basic features like windshields or well-constructed cockpits. The drivers were daring young men, eager to push these primitive vehicles to their limits in pursuit of fame and glory. Over time, the sport evolved, becoming more regulated, and today, every race is overseen by a governing body that enforces strict rules and regulations.
The following list highlights ten of the most legendary races, presented chronologically, that played pivotal roles in the evolution of motorsport.
10. The Gordon Bennett Races 1900
The first international race series was envisioned by the eccentric James Gordon Bennett Jr., the wealthy owner of the New York Herald. In 1899, Gordon Bennett offered a trophy to the Automobile Club de France, with the condition that it be contested annually by automobile clubs from various European nations. The rule required that every component of a competing vehicle, including the wheels, be manufactured in the country it represented. The inaugural race took place in 1900, running from Paris to Lyon, and was won by French driver Fernand Charron in a Panhard-Levassor. Out of the six races held between 1900 and 1905, four were sprint races (city-to-city), while the races of 1903 and 1905 featured circuit racing, held in Athy, Ireland, and Circuit d’Auvergne, France. This marked the early days of organized circuit racing, which would evolve into the Grand Prix. France dominated the Gordon Bennett races, winning four out of the six events. The other two races were claimed by a British Napier (1902) and a German Mercedes (1903).
The Vanderbilt Cup, introduced in 1904 by William Kissam Vanderbilt Jr., an American auto enthusiast, was designed to emulate the burgeoning European motor racing scene. Despite facing legal and political obstacles, Vanderbilt overcame these challenges and created an event that became a pivotal moment in American racing history. The cup's races, initially hosted on Long Island from 1904 to 1910, were among the most exhilarating events of their era. The competition helped to highlight the first wave of successful racing cars, such as the Locomobile and the Lozier. Following several venue shifts, including locations in Wisconsin, Santa Monica, and San Francisco, the event was suspended in 1916 due to the onset of World War I. It was revived in 1936, thanks to the sponsorship of Vanderbilt’s nephew, George Washington Vanderbilt III, with a 300-mile race at Roosevelt Raceway. However, due to a lack of competitive entries and a dull race format, the revived race was discontinued after only two years. The Vanderbilt Cup returned in 1960 and continued until it was integrated into the Bridgehampton Sports Car Races in 1968.
The Vanderbilt Cup, founded in 1904 by American automobile enthusiast William Kissam Vanderbilt Jr., aimed to bring the same competitive racing spirit to the United States that was flourishing in Europe at the time. Although the race faced political and legal challenges, Vanderbilt succeeded in establishing the event, which became a cornerstone of American auto racing. Held on Long Island, the early races from 1904 to 1910 were some of the most thrilling in the sport's history. The Vanderbilt Cup showcased the rise of pioneering racing cars such as the Locomobile and Lozier. After several venue changes—from Long Island to Wisconsin, Santa Monica, and San Francisco—the race was paused in 1916 due to America's involvement in World War I. The event was revived in 1936, sponsored by Vanderbilt’s nephew, George Washington Vanderbilt III, with a 300-mile race at the new Roosevelt Raceway. However, the revival faltered due to a lack of competition and a monotonous race format, leading to its cancellation after two years. The race was held again in 1960 and continued until 1968 before merging with the Bridgehampton Sports Car Races.
The Targa Florio, a legendary race that spanned from 1906 to 1977, became a symbol of Italian motor racing. The event, initially held on the winding roads of Sicily, gained fame for its grueling course and unique combination of speed and endurance challenges. Over the decades, the Targa Florio attracted some of the best drivers and cars in the world, cementing its place in racing history. While it began as a race for cars to showcase their performance on the public roads, it later evolved into a more formalized competition, attracting teams from all over the world. Its long legacy remains intertwined with the development of road racing and continues to inspire motorsport fans to this day.
The Targa Florio, established in 1906 by Italian racer Vincenzo Florio, is one of the oldest and most revered endurance road races. Held on a grueling 72-kilometer circuit, the Circuito Piccolo delle Madonie, the race wound through the mountainous regions surrounding Sicily. The first event, consisting of three laps, tested the limits of both car and driver, navigating treacherous roads and steep curves in unpredictable weather conditions. Alessandro Cagno triumphed in the inaugural race. By the mid-1920s, the Targa Florio had become one of Europe's most prominent races, predating the creation of events like the 24 Hours of Le Mans and the Mille Miglia.
In 1955, the Targa Florio joined the FIA World Sportscar Championship, propelling it to even greater heights. The race became a battleground for the world’s greatest drivers, as they competed fiercely against renowned Italian champions. The event saw intense rivalries, such as between Juan Manuel Fangio and Stirling Moss of Britain, and Tazio Nuvolari and Alfieri Maserati of Italy. The last international edition of the race took place in 1973, with a Porsche 911 prototype taking the win. Although the Targa Florio continued until 1977 as a national event, a tragic crash led to its cessation. The Porsche 911 convertible model was named 'Targa' in honor of its remarkable success at the event.
The Peking-Paris Race, held in 1907, remains one of the most legendary feats in motorsport history. The race, spanning from Peking (now Beijing) to Paris, was an unprecedented test of endurance and skill, as competitors faced harsh terrains and unpredictable challenges across vast distances.
The inspiration for one of the most famous vintage car races came from a bold 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. We ask this question of car manufacturers in France and abroad: Is there anyone who will undertake to travel this summer from Peking to Paris by automobile? Whoever he is, this tough and daring man, whose gallant car will have a dozen nations watching its progress, he will certainly deserve to have his name spoken as a byword in the four quarters of the earth….”
The race, a colossal journey spanning two continents and 15,000 kilometers, was unimaginable at a time when automobiles were still being questioned as a substitute for horse-drawn carriages. Despite the skepticism, forty entries were received, though only five brave participants committed to shipping their cars to Peking (modern-day Beijing). Among them were a Dutch Spyker, a French Contal 3-wheeler, two French DeDion cars, and an Italian 120 hp Itala, driven by Prince Scipione Borghese.
Following a telegraph route, each vehicle had a journalist aboard to document the race from within the cars. The uncharted areas of Asia, where motor travel was unheard of, proved to be a formidable obstacle. The crews faced numerous challenges, including a wooden bridge collapse that trapped the Itala, while some cars were hauled through treacherous landscapes using ropes. They got stuck in quicksand, and others limped along on benzene fuel. The Contal 3-wheeler became stranded in the vast Gobi desert and eventually gave up, though the crew was later rescued by locals.
After months of daring feats, the cars finally reached Paris, with Borghese’s Itala in the lead, several days ahead of the Dutch Spyker in second place.
The 1907 Peking-Paris Race was a pivotal moment in automotive history. It shattered all misconceptions about motor cars and demonstrated to the world that automobiles were here to stay. The race gained legendary status and was recreated multiple times, including a notable reenactment featuring 126 classic vintage cars to commemorate its centennial. The Peking-Paris Race of 1907 was more than just a competition—it became known as the greatest driving adventure of all time.
6. The New York-Paris Race, 1908
While the 1907 Peking-Paris race demonstrated that automobiles were here to stay, the 1908 New York-Paris race aimed to crush the last doubts about their viability. From Times Square, on a cold February morning, six cars representing four countries embarked on the first-ever round-the-world automobile race. The journey was grueling, with minimal paved roads ahead. As a result, drivers often found themselves using balloon tires to navigate railway tracks for miles on end when the road disappeared. The original route was planned to take them to Alaska, where the cars would be shipped across the Bering Strait. However, the intense cold forced a detour through Seattle and then onward by ship to Yokohama, Japan.
In Japan, motoring was a novel concept, particularly in rural regions. The drivers were often met with curious locals who had never seen a car. From Japan, the route continued north to Vladivostok in the Siberian tundra, where progress slowed dramatically. In fact, the speed of the race was measured in feet per hour rather than miles. After enduring this slow and painful stretch across three continents, the drivers finally reached the familiar roads of Europe. The winner, the American Thomas-Flyer, reached Paris on July 30th, four days behind the German Protos. The German team was penalized with a 30-day deduction for failing to complete the Alaskan portion of the journey before crossing the Pacific. George Schuster, the winning driver, was inducted into the Automotive Hall of Fame in 2010.
5. Indianapolis 500, 1911-present
Regarded as 'The Greatest Spectacle in Racing,' the Indy 500 made its debut in 1911 and continues to be held annually, usually on the final weekend of May. The event takes place at the perfectly oval Indianapolis Motor Speedway, located in Indianapolis, USA. Known as one of the most prestigious racing events, the race is renowned for witnessing some of the fastest speeds ever achieved in circuit racing, with cars reaching over 320 kilometers per hour as they soar around the track.
Although racing had taken place at the Indianapolis Motor Speedway prior to the Indy 500, the inaugural race (which takes its name from the 500-mile distance – around 200 laps of the track) was claimed by Ray Harroun, driving a Marmon Model-32 Wasp. His victory was met with skepticism, as he was the first to compete without a riding mechanic, who would typically assist with monitoring the oil pressure and warn of approaching cars. The allure of the substantial prize money ($50,000 in 1912) drew interest from across the globe, including established European manufacturers like Fiat and Peugeot. Over time, the race saw changes, with engine sizes being regulated according to European standards, with limits of 3 liters from 1920-22, 2 liters from 1923-25, and 1.5 liters between 1926-29.
In the aftermath of the two world wars, the future of the Indianapolis Motor Speedway appeared grim. The track was left abandoned, overtaken by weeds, and in such a state of disrepair that professional racing seemed impossible. However, local businessman Tony Hulman stepped in, reviving the track, restoring the Indy 500, and helping to usher in the golden age of post-war American motorsports.
4. 24 Hours of Le Mans, 1923-present
The iconic 24 Hours of Le Mans is the oldest and most celebrated endurance race in the world, held annually. Originally conceived as a test for the efficiency and durability of production cars, it takes place at the Sarthe Circuit in Le Mans, France. Over time, nearly every renowned automobile manufacturer has participated. The race has also been a battleground for intense personal rivalries and fierce professional competition, with the 1960s standing out as particularly significant. Henry Ford, frustrated by his failed bid to purchase Ferrari, made a pledge to defeat Ferrari on the racetrack, pouring vast resources into creating race-winning machines. The event has witnessed some of the most legendary cars in history, including the Ford Mark IV, the Ferrari 250 GTO, the Porsche 917, and the Chevrolet Corvette.
The 24 Hours of Le Mans introduced a new race format known as the 'Le Mans start.' In this exciting spectacle, cars were lined up along the pit wall, and at the signal of a waving flag, drivers would rush to their vehicles, start the engines, reverse, and begin the race – all without external assistance. This chaotic and dramatic start became an unforgettable feature of the event, but was eventually abandoned due to safety concerns, as drivers often began the race without fastening their seatbelts.
Today, the 24 Hours of Le Mans challenges competitors to cover more than 5000 kilometers from start to finish – roughly eighteen times the distance of a typical Formula 1 Grand Prix.
3. The Carrera Panamericana, 1950
The Carrera Panamericana was a legendary road race through Mexico, originally conceived to showcase the newly finished Mexican portion of the Panamericana Highway. The inaugural race, which spanned nine stages over five days, covered nearly 3300 kilometers, stretching from the northern to the southern edge of Mexico. However, after just two years, it became infamous as one of the most dangerous races ever, due to the challenging terrain, sharp turns, and drastic elevation changes—ranging from just 328 feet to an astounding 10,500 feet above sea level. To cope with the thinner air at high altitudes, cars had to adjust their carburetors. The first race was won by Hershel McGriff and Ray Eliot in an Oldsmobile. Iconic cars like the Mercedes-Benz “Gullwing” 300 SL and the Porsche 550 Spyder found success in the event. Porsche, in particular, dominated the class wins, further proving the reliability of their cars, many of which had roots in the VW Beetle. However, following a tragic crash at Le Mans in 1955, the Carrera Panamericana and similar road races were canceled. The event was revived in 1988 by Eduardo de León Camargo and continues to take place today.
Porsche commemorated their successes in the Carrera Panamericana by naming two of their vehicles after the race: the Carrera and the Panamera tourer, both inspired by their triumphs in the event.
2. Monaco Grand Prix, 1929-present
The Monaco Grand Prix, regarded as the most prestigious and popular event in the Formula 1 calendar, is often grouped with the 24 Hours of Le Mans and the Indy 500 as part of the unofficial 'Triple Crown of Motorsport'. Since 1929, the Circuit de Monaco has been the stage for this iconic race, earning a reputation for being 'an exceptional location of glamour and prestige'.
Before the inaugural Monaco Grand Prix in 1929, racing circuits were typically located in rural areas or on dedicated racetracks. The Monaco Grand Prix, however, broke this mold by taking place on the tight, winding streets of Monte Carlo, which included a tunnel. The course’s complexity demanded exceptional maneuverability from the cars. Early editions of the race were dominated by the nimble Bugattis, but in the 1930s, the more powerful Alfa Romeo 8C Monza took over.
Ayrton Senna, widely regarded as one of the greatest drivers of all time, holds the record for the most victories at Monaco, with six wins, including an impressive streak of five consecutive victories from 1989 to 1993.
1. The Mille Miglia, 1927-1957
The Mille Miglia is often considered the final chapter of the legendary road races. It was initiated in 1927 by the passionate Italian car enthusiast Count Aymo Maggi, who participated in the first race himself, driving an Isotta Fraschini 8A SS. The race, which started and ended in Brescia, covered a grueling thousand miles across the Italian countryside. Though it featured some of the most iconic Italian grand tourer brands, including Maserati, Isotta, Fiat, Ferrari, and Alfa Romeo, the Mille Miglia was canceled in 1957 after a tragic crash claimed the lives of Ferrari driver Alfonso de Portago, his co-driver Edmund Nelson, and nine spectators, including five children.
