Trail delle Cantine is a late-season trail running series in Valtellina, featuring three races that traverse vineyards, old villages, and active wine cellars. The distances offered are 13 km with 550 m of elevation gain, 21 km with 900 m, and 42 km with 1,750 m. Participants can select a shorter mountain run or a full marathon-distance trail race.
The course connects wine regions with local history, passing sites like the Basilica della Madonna di Tirano, Torre de li Beli Miri, Palazzo Besta in Teglio, Santa Casa in Tresivio, and Castel Grumello in Montagna in Valtellina. It attracts running enthusiasts from the region, concludes in the center of Sondrio, and maintains its wine focus through cellar visits and tastings associated with the event.