Gear up for a costumed joyride through Tuscany – handlebar mustache optional

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Alfredo Sosa/Staff
WHEELIE SCENIC: The author rides up to Brolio Castle in 2024 on a limestone road near the village of Madonna a Brolio.

Several years ago, I found myself staring at my 30-year-old unused bicycle with a sense of nostalgia.

Wouldn’t it be great to hop on it again? To dust off its cobwebs and go back to my earlier days of carefree riding?

When I learned about L’Eroica, an annual cycling event that begins and ends in the Tuscan community of Gaiole in Chianti, I knew where I could find people who would understand my drive. For a few days every year, the normally sleepy locale turns into a show of cosplay on vintage wheels. It’s overrun by thousands of people riding old-time bikes, often while donning outfits and facial hair (think handlebar mustaches) from their chosen historical period. (The era of my youthful joyriding, my mullet flying in the breeze, was the ’80s. Don’t judge!)

Why We Wrote This

Operating aging but cool-looking equipment in vintage clothing? For L’Eroica cyclists, that’s pure bliss.

For the eroici (Italian for “heroes”), there’s genuine joy in operating aging equipment in cumbersome clothing, even if it detracts from their performance on the road. I have participated in the event four times since 2018 and plan to return as often as my body will allow.

Alfredo Sosa/Staff
TIME MACHINE: A cyclist rides a bike from the 1930s along the 2024 L’Eroica route. The most period-faithful “eroici” (Italian for “heroes”) don’t wear helmets or any item that wasn’t in use in the era they embrace.

The approximately 209-kilometer (130-mile) route, done in large part on dirt roads, is demanding for recreational cyclists like me. Most of us start well before sunrise and finish in the dark of night. Along the way, we make friendships and experience all the beauty of Tuscany, with its limestone roads lined with Mediterranean cypress trees, its hilltop medieval towns that look like movie sets, and, of course, its gorgeous, sweeping vistas.

At the end of the day, like many other eroici, I always leave this enchanting place not thinking of my performance or my old two-wheeler. Instead, I have gratitude for having bonded with my tribe while cycling through a bit of history.

Alfredo Sosa/Staff
HAPPY TRAILS: Riders conquer a hill as the sun rises on the outskirts of Siena, Italy, during the 2024 L’Eroica event.
Alfredo Sosa/Staff
HISTORY REPEATS: Participants in period outfits hang out in Gaiole in Chianti during the 2022 L’Eroica. The annual ride began in 1997.
Alfredo Sosa/Staff
BESPOKE CYCLIST: Reenactors (not riders) pose with a penny farthing, a type of bike popular in the late 1800s, during L’Eroica festivities in 2018.
Alfredo Sosa/Staff
THRILLS IN THE HILLS: Fonterutoli, in the Castellina in Chianti area, is seen during the 2024 L'Eroica.
Alfredo Sosa/Staff
STRONG TO THE FINISH: Riders rejoice in Gaiole in Chianti after completing the 2018 L’Eroica. The ride starts and ends there.

For more visual storytelling that captures communities, traditions, and cultures around the globe, visit The World in Pictures.

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