“Some of the drives I’ve done have been a complete nightmare – but absolutely thrilling at the same time,” says Paolo Cattagni, a luxury brand director from Milan. “After all, you’re driving along 2,500m-high passes, down very narrow roads, really feeling the connection between the car and the surroundings without any filters. It’s a really engaging experience that sometimes means you have to fight with Mother Nature. You manage.”

Or, at least, some do. Unsurprisingly, not every one of the 70 or so two-person teams that take part in Italy’s WinteRace every spring make it to the end. This is a 400 km, two-day road rally that departs from Cortina d’Ampezzo, criss-crosses the Dolomites, takes five mountain passes, climbs vertiginous, little-known roads, and comprises 60 time trials, before returning to the ski resort for a parade and gala dinner.

Sure, around 25 of those teams will drive modern – if very rare – motors: Maseratis, Lamborghinis, Ferraris and, in 2013, plenty of Aston Martins. They have the advantage of power-steering, ABS and heating. But the other teams drive vintage cars; mostly pre-1976, some much older. Taking part in this year’s edition was a 1955 Porsche 356 Speedster; a 1957 Fiat 1100; a 1972 Mini Cooper; a 1925 OM 665 Sport; and a 1927 Bugatti T37. Those latter two cars are open-top.

“I’ve done the WinteRace in a vintage car without a roof,” says Cattagni. “I can tell you that at -10°C you really feel it. Especially after 10 hours of driving.” The 2023 rally was Cattagni’s sixth WinteRace, although he took part in a rather more comfortable Aston Martin DB707 SUV. “In an open-top vintage car you finish the day not being able to feel half of your body. You’re having a kind of transcendental experience. But you’re also aware that you’re alone in an old car, and at that altitude you really see the carburettor struggle. I don’t know how some cars make it. I’m not brave enough to do it in a pre-war car myself.”

Black ice. Snow drift. Freezing fog. The conditions under which the WinteRace is conducted – some of which must make for hefty insurance quotes for the seriously valuable vehicles – are all part of the fun. Established just 10 years ago, the rally – in which each segment must be driven in a specific time and at a specified average speed – has, arguably, become the chicer, more challenging alternative to Italy’s more famous Mille Miglia. It’s certainly earned a reputation as one of Europe’s most eccentric of autophile events.

The hard driving is softened with stops at Michelin-starred restaurants, a coffee break at the Italian confectioners Loacker, and a rest stop within the historic Novacella Abbey. After which there is the concourse event and gala dinner at Cortina d’Ampezzo’s Grand Hotel Savoia – the only five-star hotel in the town, it is said to have been the inspiration for Wes Anderson’s The Grand Budapest Hotel.

“Managing the often bizarre weather conditions makes the WinteRace a new experience for the drivers,” says Rossella Labate, a one-time official navigator for Alfa Romeo. Labate has been a vintage car obsessive since her father took her to see a rally at the Duran Pass in San Martino di Castrozza as a child. Labate is a veteran of the Mille Miglia; in 2012 she won the Ladies’ Cup. She also helped co-create the WinteRace a decade ago.

Labate describes the event as “the perfect mix of sports activity, culture and luxury vacation.” She believes the rally had to achieve that magical mix in order “to gain recognition and credibility.” The 2023 edition drew teams from as far afield as Scotland, Mexico and Chile. The rally remains an insider-ish event. But expect that to change after 2026, when this region of Italy hosts the Winter Olympic Games.

“I know the territory, of course, the landscape and the roads very well,” says Labate, who lives locally. “That makes organising the route each year very simple – though it still takes four months. We have to check the route multiple times in the run-up to the event, which is why we only print the road book a month before. And even then we have to have alternative B, C and D routes, just in case there’s a sudden heavy snowfall.”

In 2023, an unusually warm winter meant that most of the roads were clear. Sudden changes in the weather, however, only test drivers harder. “Sure, the conditions can be challenging in the ways that other classic road races are not, but that’s all part of the appeal,” says Alessio De Angelis, CEO of vintage car restorer, Promotor Classic. De Angelis won this year’s Category Race in a 1927 Bugatti that once belonged to Jack Lemon Burton, who helped found the Bugatti Owners Club back in 1929.

“I enjoy driving in poor-grip conditions – gravel or snow,” says De Angelis. “To be able to drive this kind of car in rain, or on the ice, isn’t easy – but it’s great fun.” De Angelis happens to be an ex professional rally raid driver, so he knows what it’s like to take on tricky terrain. “The secret is to make sure you pay attention to any feedback you can get from the car – to drive not just with your hands on the steering wheel but with your bottom on the seat. The WinteRace is a rally that gets more beautiful every year. It just has this really special glamour about it.”

The 2024 edition of WinteRace will take place from 7 March to 9 March 2024, visit winterace.it

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