Vintage Bikes, Crazy Costumes and Regular Stops for Wine & Cheese: Is This The World’s Best Bike Race?

The enduring appeal of Italy's l'Eroica Storica

Words by Ellie Ross

“You know, this has to be the only cycling event where you end up fatter than when you started.” Pushing my vintage road bike up a ridiculously steep gravel path in Tuscany, I wasn’t entirely sure I believed Alessandro Nico.

We’d only just met, but bonded by our retro steeds, woollen outfits and the gradient ahead, my fellow cyclist and I had struck up a conversation after hopping off our bikes at the same spot to tackle the slope on foot.

Sweat was trickling off my chin, my lungs were heaving and my thighs felt as though I’d stuck forks in them. Slogging next to me, Alessandro straightened his cap and continued to spur me on upwards, despite his own laboured breathing.

How were we putting on weight doing this?

“There’s a food and wine stop at the top of this hill,” he panted. “It’s the best one yet, and worth the slog.”

Bone Shaking White Roads

I had come to Chianti to take part in L’Eroica, a period bicycle ride around the region’s vineyard-cloaked hills, fuelled by good local produce. The event – which takes place on the first Sunday in October – celebrates the golden era of cycling, before the days of Lycra and carbon frames. Riders dress in classic kit – woolen jerseys, small peak caps and leather cycling shoes – and use vintage bikes.

To qualify as ‘vintage’, the bike must have been built before 1987, have gear shifters on the down tube, and pedals with toe cages instead of modern cleats. The frame must be like your nerves: made of steel.

Much of the course is made up of bone-shaking ‘strade bianche’, the gravelly white roads that crisscross Tuscany. When L’Eroica was first held in 1997, with just 92 riders, it was intended to help save these iconic roads from being gradually replaced with asphalt. And it worked. Seventeen years on, the route is marked with permanent signs and the hundreds of kilometres of bumpy, potholed tracks still exist.

But they make for difficult cycling terrain – the rough, slippery surface can rip tyres and cause crashes, and there are no support vehicles. It’s for good reason that the name ‘L’Eroica’ translates as ‘the heroic’.

Like the other 5,620 entrants to this year’s race, I feel something of a kinship with legends from a bygone era, like Eugène Christophe. The Frenchman snapped his bike’s fork in the 1913 Tour de France.

Back then there were no replacement bikes and no support cars. So Christophe walked 10km with it on his shoulder, welded it back together at a blacksmith’s and simply carried on.

Fuelling Up for the Big Day

In fairness, the race we’re riding is nowhere near as gruelling as Le Tour. The routes are divided into distances to suit all level of riders – 38km, 75km, 135km and, for the truly hardcore, 205km.

I opted for the 75km route, figuring that it would be long enough to cause some heroic suffering, but short enough to complete by dinner time.

The race starts and finishes in Gaiole, and the village undergoes a complete transformation for L’Eroica. Traders from all over Italy set up stalls selling everything from antique leather helmets, to classic goggles, retro jerseys and vintage bike parts.

The evening prior to the ride, I fuelled up with some 500 other riders at a ‘Hero’s Dinner’ in a large marquee just off the main square. Sitting at long wooden tables fit for a banquet, we feasted on a five-course meal, including bruschetta drizzled with local olive oil, a tomato and bread soup known as pappa al pomodoro and heaps of Ragu pasta, all washed down with a glass of good local Chianti.

Sitting next to me was Paul Viner, an Australian who had made the 27-hour journey from Brisbane to take part in his first Eroica. A friend had told him about the event in 1997, and he vowed to do it, but never quite managed until now.

“I was in the Queensland road racing team until I got injured,” he told me as one of the local volunteers cleared away our plates.

“My coach used to talk about the Italian giros and the spirit of what cycling was really like in the old days of gravel roads, obsolete bikes and woollen jerseys.

“The cycling heroes we are remembering were fed fruit, salami and wine in their races, then went on their merry way again. This event is set up like that and it’s so special to be part of it.”

Wacky Races

I was staying less than 10km away from the start line at La Stalla, a beautifully converted stone stable in the hamlet of Montebuoni, a two-hour drive east from Pisa airport. Once a wine and olive oil farm, Montebuoni is now made up of a handful of apartments, a pool, tennis court, private chapel and a cellar dating back to the 1500s.

From my bedroom window, neat rows of vines, heavy with purple fruit, stretched into the distance, soaking up autumn’s last rays. The next morning, I rolled down to the start line on my neon yellow and electric blue steed, hired through villa rental outfit To Tuscany.

The cobbled streets of Gaiole were crammed with cyclists in bright jerseys, waiting, impatient and still, like a multi-coloured snake ready to attack. People were chatting nervously, comparing bikes, shoes, moustaches. A cheer erupted from the back of the pack for no apparent reason, a car horn blared.

I edged towards the metal barrier start line with an energetic Austrian chap called Gerald, who was riding his third Eroica. He had woken up at 2am on the day online registration opened to ensure his place. “It’s such a friendly event,” he said, explaining L’Eroica’s appeal. “It’s like going for a Sunday bike ride with 6,000 people you haven’t met yet. “Riders wear a number but it’s not a race. It’s about enjoying yourself on a bike with good food, good company and good scenery along the way.”

We set off in staggered groups, cheered on by the large crowds that gathered early and stuck around all day. I pedalled past a man on a penny farthing with a string of sausages slung across his shoulders. To my left, a man was dressed as a vintage postman, complete with navy blue uniform, cap and a battered umbrella strapped to his pannier.

“Ciao!” he shouted, waving at me as I overtook, revealing a broad smile beneath his thick grey moustache. There was also a bloke dressed as Noah who had turned his bike into something that vaguely resembled an Ark, spilling with stuffed toys. I never found out why, but it didn’t seem to matter.

The Long and Winding Road

After a few miles, the familiar paved roads gave way to the gravelly strade. Now began some punishing climbing. I pushed upwards, my front wheel slipping on the chalky surface with each revolution, until I reached Castello di Brolio, the birthplace of Chianti wine and now home to a baron called Francesco Ricasoli.

I joined in with groups of riders who had paused to take photos of the red-brick castle on the horizon, overlooking slopes of vineyards and olive groves. Continuing downhill, I had to pick my lines carefully to avoid being bucked out of my saddle.

The terrain is gruelling for your bike, too. I stopped counting riders changing punctured wheels by the side of the road after the fifth.

At times the surface was so bumpy that the Chianti hills and roads became a blur of green and white as my eyeballs rattled around in my head.

But every time I felt close to collapse from the incessant climbs and juddering, respite came in the form of one of the four food stops on our route.


A lengthy ascent to the square in Radda, a town about halfway through the route, was rewarded with a much-needed sugar boost.

Mid Route Refuelling

Trestle tables, covered with red and white check tablecloths, were laden with platters of bread, some spread with Nutella, others soaked in red wine and sprinkled with sugar. Juicy red grapes, grown on the hills below us, overflowed from their crates, the freshly-washed bunches glistening in the sun.

The break fuelled me on to the worst of the uphill sections, just after Panzano, a pretty hilltop town, 51km through the route and famed for its butcher Dario Cecchini. I had just scoffed slices of crusty bread topped with Dario’s deliciously herby salami, and some not-so-delicious fish lard, when the gravelly road rose steeply.

I had to hop off, along with pretty much everyone else, including my new friend Alessandro. The chalky slope was dotted with people on foot, pushing their bikes and chatting to their neighbour. Alessandro had never done the Eroica before, but he had done his research into the food stations.

The stand was filled with cheese, meats, fruit and bread. A few cups of Chianti filled us with bravado.

It turned out he was right about the stop at the top of the hill – it was the best. A stand, manned by a handful of men and women dressed in traditional waistcoats and straw hats, was filled with cheese, meats, fruit, bread and deliciously sweet jam tarts, known as crostata.

Sitting in the shade of a tree, Alessandro and I refuelled with hearty ribolita, a local bread soup, and a few cups of Chianti filled us with bravado.

Riders who had earlier been battling to make good time stood around casually chatting and eating as the tune from an accordion player filled the air. Leaving wasn’t easy, but it was a downhill run for the last few miles as a golden light began to dip below the horizon.

Falling into a rhythm, I became more confident on the white roads, gradually picking up speed until I rolled, saddlesore but triumphant, into Gaiole. I may have had to get off and push at times, but crossing the finish line to the sound of the cheering crowd, I felt like a true vintage hero.


  • To Tuscany (0121-286 7782; at La Stalla at Montebuoni, a two-bedroom, two-bathroom villa with shared pool near Lecchi in Chianti, from £478 in total for the week.
  • British Airways (0844 4930787; flies to Pisa from Heathrow from £91 return and from Gatwick fares start from £77 return.
  • is a car hire comparison site. Find car hire at Pisa Airport for 7 days from £12 per day.
  • For more information on L’Eroica, visit their website. You can sign up for the 2015 from February 2015, but you can register your interest already here.
  • If you can’t wait until next year’s event, or fancy riding the route without the crowds, you can ride the route year round. Check out the Animatoscana website for details.
  • If you want something closer to home, check out L’Eroica Britannia, which takes place for the second time in 2015.
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