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Trail Running Calendar Toscana 2026-2027

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Explore the best trail runs in Toscana for 2026-2027! Our updated list features 32 exciting trail runs across the region. Find your next trail run in Toscana below and join the trail community at these great events!

Two days of trail running in Castiglion Fiorentino with multiple distances, dog trail and trekking across the crests and medieval routes of Val di Chio.
An endurance event around Montalcino featuring three competitive trails to 45 km and a 17.5 km non competitive walk on 20 and 21 February 2027.
Trail event in the Chianti hills around Radda in Chianti with races from 10 km to 123 km, charity bibs and a Golden Ticket opportunity for UTCC finishers.
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