Vintage cycling on the white gravel roads of the Val d'Orcia and Brunello hills
Eroica Montalcino is one of the flagship events of the Eroica movement, which originated in Gaiole in Chianti to celebrate vintage cycling and the culture of Tuscany's white gravel roads. In Montalcino, a stunning medieval village perched in the province of Siena, the event transforms the historic center into a stage of colors, dust, and passion every late May, drawing thousands of cyclists from all over the world to the heart of Tuscany.
The heart of the experience is the Sunday ride, starting from Piazza del Popolo. The tracks wind through the iconic white gravel roads of the Val d'Orcia and the Brunello hills, passing through historic villages such as Buonconvento, Bagno Vignoni, Pienza, San Quirico d'Orcia, and Castelnuovo dell'Abate. The five routes are designed for every level of fitness:
Eroica Montalcino is much more than a bike ride: it is a multi-day festival that brings the village to life with meetings, book presentations, live music, tastings of Brunello wine and local products, exhibitions dedicated to the history of cycling, and convivial moments in the neighborhoods of Montalcino. From cultural appointments and sustainability workshops to heroic dinners, the entire community joins in the celebration.
What makes the event unique is its philosophy: participants ride bicycles built before 1987, often wearing wool jerseys and vintage clothing. It is not about the stopwatch, but the "beauty of fatigue," the joy of the challenge, and respect for the landscape. Every year, the event attracts participants from over thirty nations, with a strong international presence that makes Montalcino a world capital of historical cycling.
A municipality in the province of Siena, in Tuscany, Montalcino is world-famous for its Brunello, one of Italy's most prestigious red wines. Its hills, part of the Val d'Orcia landscape recognized as a UNESCO World Heritage site, offer an incomparable backdrop: cypress trees, vineyards, clay hills, and ancient villages create the perfect setting for an event that combines sport, tradition, food and wine, and a love for the land.
The tenth edition of Eroica Montalcino celebrated an important milestone for the event, with approximately 2,500 cyclists from more than 30 countries (with Germany, Switzerland, Austria, the United Kingdom, and the United States among the most represented nations). The weekend, from May 29 to 31, alternated the great Sunday ride with cultural and convivial appointments in the historic center.
The five routes โ Lungo Eroico (approx. 153 km), Medio Val d'Orcia (approx. 96 km), Medio Crete Senesi (approx. 70 km), Brunello (approx. 46 km), and Passeggiata Eroica (approx. 36 km) โ departed from Piazza del Popolo with staggered start times. Weekend highlights included: meetings on sustainable mobility, book presentations, "Red Montalcino" tastings, the "Beard and Mustache" contest, and heroic dinners in the neighborhoods.
By car: Montalcino can be reached via the SS2 Cassia and the Brunello provincial road; during the event days, it is recommended to follow the signage and designated parking areas.
By train: the reference stations are Buonconvento and Sinalunga, which are connected by local buses; the nearest airport is Florence.
Registration for the ride is done online on the official Eroica website. Fees vary depending on the chosen route and include a race pack, refreshments along the track, and access to services. Participation in the festival's cultural events in the historic center is largely free.
Book your accommodation in Montalcino and nearby villages well in advance, especially for the event weekend. Cyclists are required to use a vintage bicycle according to the Eroica regulations.
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Piazza del Popolo
Piazza del Popolo, 53024 Montalcino