From 24 to 31 May 2026, Montalcino becomes the beating heart of vintage cycling and Tuscan lifestyle. Eroica Montalcino is not just a bike event — it’s a celebration of heritage, community, and the timeless beauty of the Val d’Orcia.
As a tour operator based in Tuscany, we love this event because it captures everything that makes our land unforgettable: slow travel, authentic encounters, great food and wine, and the magic of the strade bianche.
Sunday 24 May — EROICA JUNIORES Siena–Montalcino
The week opens with the Eroica Juniores International – Coppa Andrea Meneghelli, a prestigious U19 race that brings young athletes from all over the world onto the same gravel roads that have shaped cycling history.
The arrival in Piazza del Popolo is always emotional: cheering crowds, the award ceremony, and the first taste of the Eroica atmosphere that will fill the town for the entire week.
The Eroica Festival: Friday 29 – Sunday 31 May 2026
The true heart of the event is the final weekend, when Montalcino transforms into a vibrant open‑air festival. Lanterns made from vintage jerseys light up the medieval streets, music fills the squares, and the scent of Brunello and Tuscan cuisine drifts through the air.
Friday 29 May — Opening Day
- Vintage Market at the Fortress
- Sponsor Village in Piazza Garibaldi
- Eroica Caffè with tastings and live music
- Book presentations and cultural talks
- Photo exhibitions and creative installations
- Technical area: bike check, registration, Eroica bike certification
Saturday 30 May — Culture, Style & Tuscan Flavours
A day packed with experiences for cyclists and non‑cyclists alike:
- Vintage market & sponsor village
- Creative workshops and family activities
- Wine tastings featuring Rosso and Brunello
- Book presentations with authors and historians
- The iconic “Hair & Beard Contest” — a beloved Eroica tradition
- The Eroica Dinner in the four historic districts of Montalcino
- Music, aperitifs, and entertainment until late
Sunday 31 May — The Day of the Rides
At sunrise, Piazza del Popolo fills with wool jerseys, steel bikes, and the unmistakable excitement of heroic cycling.
Five official routes depart through the UNESCO landscapes of the Val d’Orcia:
- Long Route – 153 km
- Medium Val d’Orcia – 96 km
- Medium Crete Senesi – 70 km
- Short Brunello – 46 km
- Eroica Walk – 37 km
Throughout the day:
- Music and storytelling in the main square
- Pasta Party at the Fortress
- Celebration until the last rider arrives
- Final toast with the Eroica Team
Why Eroica Montalcino Is Truly Special
For us, Eroica Montalcino represents the essence of Tuscany: authenticity, community, tradition, and the joy of discovering beauty at a slower pace.
It’s an event for everyone:
- cyclists
- families
- wine lovers
- culture enthusiasts
- travellers seeking genuine experiences
The Perfect Moment to Discover the Val d’Orcia
Late May is one of the most beautiful times of the year: rolling green hills, warm sunsets, open wineries, and a festive atmosphere that embraces every visitor.