The Mille Miglia isn’t what it used to be and that’s a good thing. First starting in 1927, it was – for a 30-year period – the most competitive race in the world. Similar to the Targa Florio and the Carrera Panamericana, it was a race of skill, endurance and reliability. It took in 1,000 miles of Italy, beginning in Brescia and heading down to Rome and back. It wasn’t long before the major manufacturers saw it as imperative to win.

Alfa Romeo was the early dominator, winning three of the first four races. Mercedes-Benz then crashed the party, winning in 1931 before Alfa won the next seven in a row. The war came and then it was Ferrari’s turn. The great marque dominated the postwar era, with Enzo Ferrari’s all-Italian lineups becoming the pride of the nation throughout the late ’40s and ’50s. Mercedes-Benz ruined the fun again though, with Stirling Moss and co-driver Denis Jenkinson breaking a record that would never be beaten. They won the 1955 Mille Miglia, completing the 1,000-mile race in just 10 hours, 7 minutes and 48 seconds, averaging around 100mph in the process.

Two years later, in ’57, everything changed again. A horrific crash killed three drivers, Alfonso de Portago, Edmund Nelson and Joseph Göttgens – as well as nine spectators – and the Italian authorities immediately banned public racing in Italy. The crash formed the basis of the 2023 Michael Mann film Ferrari, which accurately depicted the brutality of the race.
Today, the Mille Miglia is no longer a competitive race. It’s now a regularity rally, where entrants must hit checkpoints at certain times, prioritising timekeeping and accuracy over outright speed. It isn’t as dangerous as it once was but it’s still as thrilling and remains a special event. Those who enter must do so in cars that competed in the Mille Miglia in period. That means that only models that raced between 1927-1957 can take part. The route is very similar, too: beginning in Brescia, it takes in Turin, Siena and Rome, before looping back up and finishing in Brescia.

This year, I took part with the works Mercedes-Benz team, where I co-drove a 1930 Mercedes Super Sport that was originally commissioned by the last Maharaja of Kashmir. I managed to take some photos in between sweating and trying to keep up with the 100-page road book. These are the wonderful cars, characters and spectators who make the event one of the great highlights of the motoring calendar.











Charlie Thomas is a UK-based writer, journalist and photographer. He has written for the Financial Times How To Spend It, GQ, The Times, Robb Report and The Independent



