Motor racing traces its roots back to the very first motorised automobiles. In those early days, the sport looked nothing like the high‑tech spectacles we see today. Cars were massive, fuel‑hungry beasts with modest power, often unreliable and prone to breaking down at a moment’s notice. Many lacked even the most basic comforts such as windshields or proper cockpits. Yet a daring generation of young, fearless drivers pushed these machines to their limits in pursuit of glory and the thrill of speed. As the sport matured, it underwent dramatic transformations, faced legal constraints, and eventually fell under the watchful eye of governing bodies that enforce strict rules and regulations.
10 Historic Car Races That Shaped Motor Racing
10 Gordon Bennett Races
The first truly international race series ever conceived was the brainchild of the flamboyant James Gordon Bennett Jr., a millionaire publisher of the New York Herald. In 1899, he offered a trophy to the Automobile Club de France, stipulating that it be contested annually by automobile clubs from various European nations. A unique rule required every component of a competing vehicle to be manufactured in the country it represented, wheels included. The inaugural race in 1900 ran from Paris to Lyon and was won by Frenchman Fernand Charron behind the wheel of a Panhard‑Levassor. Between 1900 and 1905, six races were held; four were sprint‑style city‑to‑city events, while the 1903 and 1905 editions were circuit races at Athy in Ireland and the Circuit d’Auvergne in France. This series also marks the earliest recorded instance of organised circuit racing, a format that later evolved into the Grand Prix after 1905. France dominated the Gordon Bennett contests, securing four victories, while Britain’s Napier claimed a win in 1902 and Germany’s Mercedes triumphed in 1903.
9 Vanderbilt Cup
While a myriad of independent racing series were sprouting across Europe in the first decade of the twentieth century, American auto‑enthusiast William Kissam Vanderbilt Jr. wanted to spark a similar boom stateside. In 1904 he launched the Vanderbilt Cup, an international competition open to entrants from any nation. The race’s announcement sparked political and legal controversy, as many tried to block its realization, but Vanderbilt persisted. The Cup quickly became the first major trophy in American auto racing history. Early editions (1904‑1910) were held on Long Island and delivered some of the era’s most exhilarating contests. Iconic early winners included the Locomobile and the Lozier. After 1910 the venue shifted to Wisconsin, then Santa Monica, and later San Francisco, before the United States entered World War I in 1916, causing the race’s suspension. A revival came in 1936 when George Washington Vanderbilt III sponsored a 300‑mile event at the newly built Roosevelt Raceway, but lackluster competition and a dull format led to its abandonment after just two years. Another revival occurred from 1960‑1968 before the Cup merged with the Bridgehampton Sports Car Races.
8 Targa Florio
One of the world’s oldest endurance road races, the Targa Florio was founded in 1906 by Italian racer Vincenzo Florio. The competition wound around the 72‑kilometre Circuito Piccolo delle Madonie, traversing the rugged Sicilian mountains. The first edition featured three laps of treacherous, winding roads, with Alessandro Cagno taking the victory. By the mid‑1920s the Targa Florio had eclipsed both the 24 Hours of Le Mans and the Mille Miglia, which were not yet established. In 1955 the race joined the FIA World Sportscar Championship, attracting legends such as Juan Manuel Fangio, Stirling Moss, Tazio Nuvolari and Alfieri Maserati. The event’s final world‑championship edition came in 1973, won by a Porsche 911 prototype, and it continued as a national race until 1977, when a fatal crash forced its cessation. Porsche later honoured the event by naming its iconic Targa model after the race.
7 Peking‑Paris Race
The legendary Peking‑Paris challenge originated from a daring editorial in the Paris newspaper Le Matin, which asked manufacturers whether a man could traverse the globe by automobile. The 1907 contest spanned two continents and covered roughly 15,000 km, a feat unimaginable when most still relied on horse‑drawn carriages. Forty teams entered, but only five actually shipped their machines to Peking (today’s Beijing): a Dutch Spyker, a French Contal three‑wheeler, two French De Dion cars, and an Italian 120 hp Itala driven by Prince Scipione Borghese. Each car carried a journalist as a passenger to chronicle the journey. The route followed the telegraph line, exposing crews to extreme hardships: wooden bridges collapsed, quicksand trapped vehicles, and some cars were refuelled with benzene. The Contal 3‑wheeler succumbed to the Gobi Desert and withdrew, while the Itala endured a broken bridge and rope‑hauling. After months of perilous adventure, the Itala crossed the finish line in Paris ahead of the Spyker. The race shattered doubts about the automobile’s viability and has been re‑enacted several times, most recently with 126 classic cars celebrating its centenary.
6 New York‑Paris Race
Following the Peking‑Paris triumph, the 1908 New York‑Paris race was conceived as the ultimate proof‑of‑concept for the automobile. Six cars from four nations set off from Times Square on a frosty February morning. With few paved roads, competitors often rode balloon‑tired machines atop railway tracks for hundreds of miles when no road existed. The original plan called for a trek to Alaska, with a ship across the Bering Strait, but brutal Alaskan cold forced a reroute through Seattle and a trans‑Pacific shipment to Yokohama, Japan. In Japan, the drivers encountered astonished locals who had never seen a car. From there the route continued north to Vladivostok, then across Siberia’s tundra, where progress was measured in feet per hour. After a grueling three‑continent odyssey, the competitors finally reached Europe. The American Thomas‑Flyer arrived in Paris on 30 July, four days after the German Protos, but the Germans were penalised 30 days for skipping the Alaskan leg, awarding the victory to the Thomas‑Flyer. Its driver, George Schuster, was inducted into the Automotive Hall of Fame in 2010.
5 Indianapolis 500
Dubbed the “Greatest Spectacle in Racing,” the Indianapolis 500 debuted in 1911 and remains an annual May tradition. The race takes place on the iconic oval of the Indianapolis Motor Speedway in Indiana, covering 500 miles (200 laps). The inaugural winner, Ray Harroun, piloted a Marmon Model‑32 “Wasp” and famously completed the entire event without a riding mechanic—a bold move that sparked controversy. The prize purse, $50,000 in 1912, attracted global manufacturers, including European marques such as Fiat and Peugeot. Over the years the event’s engine regulations shifted: 3‑liter limits (1920‑22), 2‑liter (1923‑25), and 1.5‑liter (1926‑29). After both World Wars, the Speedway fell into disrepair, overgrown with weeds. Entrepreneur Tony Hulman revived the venue and the Indy 500, ushering in a golden age for American motor sport.
4 24 Hours of Le Mans
The 24 Hours of Le Mans stands as the oldest and most prestigious endurance race still contested today. First held to test the reliability and efficiency of production cars on the Sarthe circuit in France, the event quickly attracted every major marque. The 1960s saw fierce rivalries, most famously between Henry Ford’s determination to defeat Ferrari and the Italian giant’s dominance. Iconic winners included the Ford Mark IV, Ferrari 250 GTO, Porsche 917, and Chevrolet Corvette. Le Mans also introduced the famous “Le Mans start,” where drivers sprinted to their cars, jumped in, started engines, and drove off without assistance—a practice later banned for safety reasons. Modern editions see competitors covering more than 5,000 km, roughly eighteen times the distance of a typical Formula 1 Grand Prix.
3 Mille Miglia
The Mille Miglia, launched in 1927 by Italian enthusiast Count Aymo Maggi, was arguably the last great road‑race of its era. Starting and finishing in Brescia, the event covered a thousand miles of Italy’s scenic countryside, showcasing the nation’s finest grand‑tourer marques—Maserati, Isotta‑Fraschini, Fiat, Ferrari, and Alfa Romeo. The race met a tragic end in 1957 after a fatal crash that claimed Ferrari driver Alfonso de Portago, his navigator Edmund Nelson, and nine spectators, including five children. The catastrophe led to the event’s cancellation, marking the close of an iconic chapter in motor‑sport history.
2 Monaco Grand Prix
The Monaco Grand Prix, first run in 1929, is arguably the most glamorous and prestigious stop on the Formula 1 calendar, forming part of the sport’s unofficial “Triple Crown” alongside Le Mans and the Indy 500. Unlike earlier Grand Prix events held on purpose‑built tracks or in the countryside, Monaco’s race unfolds on the narrow, twisting streets of Monte Carlo, complete with a tunnel and tight hairpins that test a car’s handling above all else. Early winners were dominated by agile Bugattis, later supplanted by the powerful Alfa Romeo 8C Monza in the 1930s. Ayrton Senna, widely regarded as one of the greatest drivers ever, claimed six victories at Monaco, including an unprecedented streak of five consecutive wins from 1989 to 1993.
1 Carrera Panamericana
The Carrera Panamericana emerged in 1950 as a spectacular Mexican road race designed to showcase the newly completed Panamerican Highway. The inaugural edition spanned nine stages over five days, covering roughly 3,300 km from the country’s northern border to its southern tip. The route’s extreme elevation changes—rising from 328 feet to 10,500 feet above sea level—forced teams to adjust carburettors for thin air. Winners Hershel McGriff and Ray Elliott piloted an Oldsmobile, while later races saw successes from the Mercedes‑Benz “Gullwing” 300 SL and the Porsche 550 Spyder. Porsche’s dominance in various classes highlighted the reliability of the VW‑based Beetle lineage. After a tragic crash at Le Mans in 1955, the race—along with other dangerous road events—was discontinued. It was revived in 1988 by Eduardo de León Camargo and continues today as a celebrated historic motorsport festival.
These ten legendary contests not only pushed the limits of engineering and human courage but also laid the foundation for the modern motorsport world we adore today.