As customary with Italian, the two words (“thousand” and “miles”) come together perfectly, gracefully rolling off the tongue. But putting phonetics aside, the Mille Miglia happens to be one of the world’s most classic automobile races, bringing images of sleek sports cars driven by equally sleek gentlemen through pittoresque villages along beautiful country roads.

Mille Miglia started out as a typical Italian affair, the idea arising from Conte Maggi and his friends, Giovanni Canestrini, Conte Mazzotti and Renzo Castagneto. As proud people of Brescia, in their minds the birthplace of Italian motorsport, they were shocked when the 1922 Italian Grand Prix was moved to the new Autodromo Nazionale Monza. It is said, after all, that fuel rather than blood flows through the veins of the people who come from Brescia.

Over dinner at the famous Vecchio Café in Milan, Maggi and his three friends laid out their response plan, arguing long into the night over the lack of sporting Italian automobiles. The four Musketeers of the Mille Miglia all believed that racing improves the breed and quickly decided on conducting a race. But not just any race! No, this race would have to be something that captured the imagination of all Italian people – from Brescia to Rome.

They realized that building a new circuit would just appear to follow in the footsteps of their Milanese rivals. Instead, a road race was suggested, one that would start in Brescia and finish in Rome. In fact, after some patriotism was thrown into the mix, it was decided that the race would be Brescia-Rome-Brescia, approximately 1600 kilometers or… a thousand miles. The Mille Miglia was born.

Between 1927 and 1957 this epic endurance race took place twenty-four times, surviving a world war and making sports cars like Porsche, Alfa Romeo, Ferrari, BMW, and Mercedes Benz famous in the process. Each and every year the average speeds increased, and unfortunately, the accidents soon followed. After claiming 56 lives in total, the race was eventually banned after two fatal crashes, including that of Ferrari driver Alfonso de Portago and nine spectators – of which five were children.

But as we all know, legends can be hard to get rid of, and twenty years later the name was revived once again. This time as the Mille Miglia Storica, a several day long historical tribute to the sports cars and drivers that once raced along this classic route. Today, the reenactment of Mille Miglia is a class of its own, full of extraordinary cars and personalities surrounded by beautiful scenery and the traditional Italian way of living.

We wouldn’t miss it for the world. We grabbed the awesome photographer and friend Oskar Bakke as well as our stainless steel Heritage 40 and headed for a race down memory lane.