Gaiole in Chianti Events

One event defines the calendar here. L'Eroica is held at Gaiole in Chianti on the first Sunday in October. The ride winds over the strade bianche that cross the landscapes of the Sienese Chianti, the Crete Senesi and the Val d'Orcia, with an eye to the past: antique bicycles, riders in vintage clothing, vintage cars and motorbikes, and wine, capocollo and pecorino at the stops.

It began here, and recently. L'Eroica was born in 1997 at Gaiole in Chianti, when 92 riders set off on the first edition. The comune records that the first seed was sown in February 1992, in an article in the Sienese magazine Mesesport proposing a "Parco Ciclistico del Chianti".

The event now carries a programme around it — a register of eroiche bicycles, a bicycle elegance competition, a Mini Eroica and children's cycling, a beard-and-moustache competition, a shop-window contest, an Eroica Academy, a sustainability manual and a free shuttle service with published parking and traffic arrangements.

Plan around it or into it, but do not ignore it. A comune of 2,454 people hosting an international ride on one Sunday is the single largest thing that happens here all year.

Verified against Visit Tuscany (Toscana Promozione Turistica), October 2026.

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Sources & verification Covers the sourced claims on this page.

Checked against Visit Tuscany (Toscana Promozione Turistica) — On the first Sunday in October the Eroica is held in Gaiole in Chianti; the cycling event winds its way through the white roads that cross the landscapes of the Sienese Chianti, the Crete Senesi and the Val d'Orcia, with an eye to the past, featuring antique bicycles, cyclists in vintage clothing, a range of vintage cars and motorbikes, as well as wine, capocollo and pecorino. (October 2026).
Checked against Eroica — L'Eroica was born in 1997 at Gaiole in Chianti, a small borgo in the province of Siena, where 92 riders set off the first edition of a cycling event that each year combines demanding routes, magnificent landscapes and memorable refreshment stops; the event publishes parking and traffic arrangements and runs a free shuttle service, alongside a register of eroiche bicycles, a bicycle elegance competition, a Mini Eroica and children's cycling, a beard and moustache competition, a shop-window contest, an Eroica Academy and a sustainability manual. (October 2026).
Checked against Comune di Gaiole in Chianti — The Comune di Gaiole in Chianti records that the first seed of the Eroica was sown in February 1992, in an article in the Sienese magazine Mesesport proposing a Parco Ciclistico del Chianti., The Comune di Gaiole in Chianti has its seat at via Ricasoli 5, 53013 Gaiole in Chianti (SI), with a switchboard on 0577 744711, a freephone number on 800 012661 and the certified address comune.gaioleinchianti@postacert.toscana.it; it lists thirteen offices, among them the URP on 0577 744743, Lavori Pubblici e Protezione Civile on 0577 744744, the Polizia Municipale on 0577 744723 and 0577 744737, and the SUAP on 0577 744738, 0577 744739 and 0577 744743. (October 2026).