L’Eroica began in Gaiole in Chianti in 1997 with just 92 cyclists and a simple idea from founder Giancarlo Brocci: celebrate cycling’s roots and protect Tuscany’s strade bianche (white gravel roads).

What started as a local, non-competitive ride has grown into a global movement, but its heart remains Tuscan: Chianti’s vineyards, the Crete Senesi, and the UNESCO-listed Val d’Orcia south of Siena. The official motto says it all: “the beauty of fatigue and the thrill of conquest.”

 

What makes L’Eroica a very challenging ride

At its core, L’Eroica Gaiole is a vintage cycling festival on the first weekend of October, mixing demanding routes and convivial food stops with old-school bikes and wool jerseys. The organization also curates a permanent route (about 209 km with ~3,800 m of elevation) so you can ride the Chianti–Crete Senesi–Val d’Orcia triangle any time of year, not only on event day.

The classic bike rules (high level): steel frames, down-tube shifters (or pre-1980 non-indexed bar-end), external brake cables, toe-clip pedals, and low-profile rims with ≥32 spokes a spec that keeps the riding feel “of the era.” (Modern Nova Eroica events are for gravel/all-road bikes.)

 

Why it’s so Tuscan

The courses stitch together hill towns, cypress lanes and wine roads; Montalcino’s southern loops cross the Val d’Orcia, a UNESCO World Heritage landscape since 2004. In Tuscany you feel the L’Eroica philosophy most clearly: effort is rewarded not just by a finishers’ stamp, but by scenery, stories and community. eroica.cc

 

The 2025/2026 calendar – confirmed and announced dates

Below is a traveler-friendly digest of Eroica (vintage) and Nova Eroica (all-road/gravel) dates drawn from the official site and event pages. Where organizers have only provided a “save the date” or “unconfirmed,” that’s noted.

Tuscany & Italy

  • L’Eroica Gaiole (Tuscany) — October 4–5, 2025
    The flagship vintage weekend in Chianti. Expect multiple route options on and off the strade bianche.
  • Eroica Montalcino (Tuscany) — May 25, 2025 (held); May 31, 2026 (announced)
    Vintage ride over the southern piece of the Gaiole long route, through Crete Senesi and Val d’Orcia.
  • Nova Eroica Gran Sasso (Abruzzo) — June 7, 2025 (held)
    The “all-road” format in Italy’s high Apennines, with timed segments and transfer sections.
  • Nova Eroica Buonconvento (Tuscany) — June 21–22, 2025 (held); June 20–21, 2026 (weekend; unconfirmed day-by-day)
    The gravel/all-road cousin to Gaiole, based in the Crete Senesi. 2025 included a Family Ride on Saturday.
  • Nova Eroica Ivrea (Piedmont) — September 14, 2025 (held)
    Canavese’s gravel and lakes in a timed-segments format.
  • Eroica Dolomiti (South Tyrol) — September 6, 2025 (held); September 5, 2026 (save the date/unconfirmed)
    Vintage roads around San Candido; a mountain-scenery twist on the classic formula.
  • Nova Eroica Prosecco Hills (Veneto) — 2025 edition held (see regulations page)
    Rolling gravel among Conegliano–Valdobbiadene vineyards; the event now features an “Epic” 220 km option. (Watch for 2026 announcement.)
  • Nova Eroica Istria (Croatia) — September 20–21, 2025 (held)
    Debut “Truffle Tour” weekend based in Novigrad/Cittanova.

 

Europe & worldwide

  • Eroica Germania (Eltville-Erbach, Rheingau) — August 23, 2025 (held); August 22, 2026 (unconfirmed)
    Three vintage routes among vineyards and castles; a full festival weekend.
  • Eroica Valkenburg (Limburg, Netherlands) — June 6–7, 2025 (held); June 5–6, 2026 (save the date)
    Vintage riding on Limburg’s punchy hills, plus a period cycling fair.
  • Eroica Japan (Naeba, Niigata) — August 23–24, 2025 (held)
    Old Bike Meeting within the Feel EARTH festival at Naeba Highland campsite.
  • Eroica Cuba (Caimito) — February 14, 2026 (unconfirmed)
    A growing outpost for the vintage format; watch the official channels for final confirmation.

Tip: organizers sometimes finalize exact start-day formats (expo, family ride, main ride) closer to the event. Always cross-check the event page on Eroica.cc before you book travel.

 

How L’Eroica shaped modern gravel culture

Brocci’s drive to preserve gravel roads didn’t just create a beloved vintage event; it also inspired the professional Strade Bianche classic. In other words, today’s white-road racing owes a debt to a Tuscan community ride that refused to let sterrato disappear.

 

Planning your own “Heroic” trip

  • Pick your format: “Classic” (vintage) = pre-1987 style bikes per the rules; “Nova” = modern gravel/all-road bikes. Tuscany gives you both: Gaiole in October (vintage) and Buonconvento in June (Nova).
  • Ride beyond race day: the Eroica permanent route lets you sample Chianti to Montalcino in stages, any month you like.
  • Understand the kit: down-tube shifters, toe-clips, external cables, and 32-spoke wheels are not “retro cosplay”; they’re how the event protects its feel and, yes, they change how you climb and descend Tuscany’s gravel.

 

If you love Tuscany and cycling with a sense of story, L’Eroica is the purest expression of both: an Italian tradition that turned gravel into heritage and fatigue into joy. Use the 2025/2026 calendar above to plan your ride whether you’re pinning a vintage number in Gaiole, chasing gravel fun in Buonconvento, or collecting stamps at far-flung Eroica festivals. The spirit is the same everywhere, but it started, and still feels most “heroic”, on the white roads of Tuscany.