Autumn is one of my favourite times of year in Anghiari. As the summer heat fades and the countryside begins to change colour, the town comes alive with a series of events and celebrations.
L’Intrepida is the first of three much-loved autumn events in Anghiari. It is followed by I Centogusti dell’Appennino, when the historic centre fills with stalls showcasing food and produce from across the Apennines, and then the Festa dei Bringoli, dedicated to Anghiari’s traditional handmade pasta.
First, though, come the bicycles.
Every October, the streets of Anghiari fill with vintage bikes, colourful wool jerseys and cyclists arriving from across Italy and further afield for L’Intrepida, one of the town’s most distinctive annual events.
Much more than a cycling event, L’Intrepida has become an important part of Anghiari’s calendar and a wonderful example of the strong sense of community that makes this corner of Tuscany such a special place to live.
What is L’Intrepida?
First held in 2012, L’Intrepida is a non-competitive vintage cycling event that takes riders through the countryside surrounding Anghiari and the Upper Tiber Valley.
The event celebrates cycling as it once was. Participants ride historic racing bicycles dating from before 1987 – it’s a slightly bitter pill to swallow when the year I turned 17 apparently qualifies as vintage, but I’m trying not to take it personally.
Many cyclists complete the look with vintage-style wool jerseys, shorts and caps inspired by an earlier era of Italian cycling.
Over the years, L’Intrepida has grown considerably. The inaugural event attracted just over 200 cyclists, while recent editions have welcomed more than 1,000 participants to Anghiari.
Cycling Through History
Part of the appeal of L’Intrepida is undoubtedly its setting.
The routes follow roads and tracks through the countryside around Anghiari, including areas associated with the Battle of Anghiari, fought here on 29 June 1440 and later immortalised by Leonardo da Vinci.
Around 40% of the routes are along strade bianche – Tuscany’s characteristic unpaved country roads – as well as farm tracks and quiet rural lanes.
Cyclists pass through a landscape of medieval villages, castles, woodland, farmland and rolling hills, with traditional refreshment stops along the way adding to the atmosphere.
There are three routes to choose from:
- Corto – 42 km
- Lungo – 85 km
- Intrepido – 118 km
The longest route certainly lives up to its name, but L’Intrepida is not about racing to the finish line. It is about enjoying the ride, the landscape, good food and the company of other cyclists.
More Than a Bike Ride
One of the things we particularly like about L’Intrepida is that you certainly don’t need to be taking part in the ride to enjoy it.
For several days, Anghiari takes on a completely different atmosphere. The historic centre fills with vintage bicycles, music, food and stalls selling cycling clothing and memorabilia, while cyclists and visitors spill into the streets, bars and restaurants.
And it isn’t only the cyclists who dress for the occasion. Plenty of local people and visitors join in too, embracing the vintage theme in fabulous 1950s-style dresses, skirts, scarves and sunglasses. Vintage Vespas and classic cars also join the fun, following the cyclists along parts of the route. My lovely father in law, Mr Lega Snr has been getting into the spirit for many years, making his annual appearance as Sherlock Holmes – by now, something of an L’Intrepida tradition in its own right. Against the backdrop of Anghiari’s historic streets, it can feel a little like stepping back in time and adds to the fun and slightly eccentric character of the weekend.
Food, as you might expect in Tuscany, is also an important part of the event. The refreshment stops are rather different from those at your average cycling event, with pasta and even wine on offer. Personally, after both, I’d be more inclined to take a nap than get back on a bicycle, but the Intrepidi are clearly made of sterner stuff.
After the ride, participants return to Anghiari for lunch, where the menu traditionally includes bringoli, the thick handmade pasta typical of the town – and the star of another of Anghiari’s autumn celebrations just a few weeks later.
It all comes together to make L’Intrepida one of the most enjoyable weekends in Anghiari’s calendar.
L’Intrepida 2026
The 14th edition of L’Intrepida takes place in Anghiari from 15–18 October 2026, with the main vintage cycling event on Sunday 18 October.
The programme extends well beyond Sunday’s ride, with events taking place in and around the historic centre throughout the weekend.
The main event begins on Sunday morning, when cyclists set off from Anghiari on the 42 km, 85 km and 118 km routes through the surrounding Tuscan countryside.
You don’t need to be a cyclist to enjoy L’Intrepida. Come along for the atmosphere, the vintage bikes and outfits, and to see Anghiari at its lively, colourful best.
Autumn in Anghiari
L’Intrepida may be the first of Anghiari’s big autumn events, but there’s plenty more to come, with I Centogusti dell’Appennino and the Festa dei Bringoli following over the next few weeks.
If, like me, autumn is your favourite time of year, you can read more about these and some of our other favourite local celebrations in our blog, Autumn in Tuscany and Umbria – The Joy of Seasonal Eating and Celebrations.
For now, though, it’s time to dust off the vintage bikes, find your best 1950s outfit and enjoy one of the most colourful weekends in Anghiari’s calendar.
