The most famous car races in history include the 24 Hours of Le Mans (first run 1923, joining the World Sportscar Championship in 1953), the Mille Miglia (Italy’s 1,600 km road race, 1927-1957), the Indianapolis 500 (first held 1911, still running annually), and the Cannonball Run (an unsanctioned 1971-1979 coast-to-coast dash created to protest strict traffic laws). Each represents a genuinely different era and philosophy of motorsport — endurance, public-road spectacle, oval-track speed, and outright outlaw record-chasing.
Here’s the history and defining moments behind each race, and why they still shape motorsport culture today.
Key Takeaways
- The Mille Miglia ended in 1957 after a crash killed a driver and at least nine spectators, leading to a ban on public-road racing in Italy.
- Stirling Moss’s 1955 Mille Miglia run at a 97.96 mph average speed is considered one of the greatest single drives in motorsport history.
- The Indianapolis 500 has run nearly every year since 1911, pausing only during the two World Wars.
- The Cannonball Run was explicitly illegal, created in 1971 partly as a protest against strict traffic laws.
A Timeline of Legendary Races
The Mille Miglia: Italy’s Most Beautiful Race
Often called the most beautiful race in the world, the Mille Miglia is one of the most famous events in motorsport history alongside the 24 Hours of Le Mans and the Indianapolis 500 (Heacock Classic). First run in 1927, its 1,600 km route from Brescia to Rome and back made it Italy’s most ambitious road race. Perhaps the most famous single drive in the race’s history came in 1955, when Stirling Moss, driving a Mercedes-Benz 300 SLR with navigator Denis Jenkinson, established a seemingly impossible 97.96 mph average speed over the full public-road course (The Gentleman’s Journal).
The race ended in 1957 after a crash killed a driver and at least nine spectators, leading to a ban on racing on Italy’s public roads — a stark reminder of how genuinely dangerous open-road racing at these speeds actually was, and why the era of racing directly through towns and countryside eventually gave way to purpose-built closed circuits.
Le Mans: Endurance Racing’s Ultimate Test
There’s no race more difficult or important than the 24 Hours of Le Mans, which became part of the World Sportscar Championship in 1953 alongside races like the Mille Miglia (Heacock Classic). Notable victories include Ferrari’s first Le Mans win in 1949 and Ford’s 1966 triumph — considered the most important American team win outside the USA, a result immortalized in popular culture for the intensity of the Ford-Ferrari rivalry behind it.
The Indianapolis 500: America’s Racing Institution
The inaugural Indianapolis 500 was held on May 30, 1911, attracting an estimated crowd of 85,000 spectators — a genuinely massive audience for a young sport at the time. Ray Harroun drove his single-seater Marmon Wasp to victory in that first race, one of 40 cars that had qualified by sustaining a speed of at least 75 mph, taking home $14,250 in prize money (Indianapolis Motor Speedway). Since 1911, the race has run every year with only two exceptions — pausing during World War I (1917-1918) and World War II (1942-1945) — making it one of the most enduring annual sporting traditions in the world.
If today’s race car engineering and speed interests you, our guide on Formula 1 facts covers the modern physics and numbers behind top-tier racing, and our guide on best race car drivers of all time covers the individuals who defined these and other legendary races.
The Cannonball Run: Racing Outside the Rules
The Cannonball Run — officially the Cannonball Baker Sea-To-Shining-Sea Memorial Trophy Dash — was created in 1971 by race car driver Brock Yates and car magazine editor Steve Smith, both to celebrate the Interstate Highway System and to protest strict traffic laws many felt infringed on driver freedom (GearJunkie). Yates and co-driver Dan Gurney won the first event in 1971 driving a Ferrari Daytona. The race continued sporadically in 1972 and 1975, with a final official running in 1979 — its explicitly unsanctioned, illegal nature on public interstates makes it a genuinely different chapter in racing history compared to the sanctioned events above.
Frequently Asked Questions
Why did road racing largely disappear after the Mille Miglia era?
The safety risks of racing at high speed through towns and unprotected public roads became increasingly unacceptable as speeds climbed, pushing the sport toward purpose-built closed circuits with proper barriers, run-off areas, and spectator protection.
Is the Cannonball Run legal to attempt today?
No — attempting a Cannonball-style record run today involves the same illegal speeding on public interstates that made the original controversial, and modern traffic enforcement, cameras, and tracking make it both far riskier and more consequential than in the 1970s.
Which of these races still exists in its original form?
The Indianapolis 500 and 24 Hours of Le Mans continue essentially in their traditional format today, while the Mille Miglia now runs as a regulated classic-car rally rather than a genuine flat-out race, and the Cannonball Run exists only as an underground, unofficial record chase.
What made these races so dangerous compared to modern racing?
Early racing lacked the safety technology — roll cages, crumple zones, barrier systems, medical response protocols — that modern motorsport takes for granted, meaning drivers and spectators alike faced genuinely higher fatality risk than today’s heavily regulated racing environments.
The Bottom Line
From the Mille Miglia’s beautiful but ultimately fatal open-road era, to Le Mans’s grueling endurance test, the Indianapolis 500’s enduring American tradition, and the outright illegal spectacle of the Cannonball Run, these races each represent a distinct chapter in motorsport history. Their legacies still shape how racing is organized and regulated today, from the closed-circuit safety standards that followed the Mille Miglia’s end to the enduring cultural weight of Indy’s Memorial Day tradition.
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