The Mostra del Chianti Classico di Montespertoli, held each June (usually the second or third weekend), is one of the oldest wine festivals in Tuscany and the main event on the Montespertoli calendar. Producers from across the Chianti DOC zone bring their wines for tasting, the town's streets fill with market stalls, and the piazza hosts cooking demonstrations and live music.
The festival has run since 1962 and draws visitors from Florence and beyond. It is a genuinely local affair rather than a tourist production — the focus is on the wine and the food rather than spectacle. Montespertoli itself produces wines under both the Chianti Colli Fiorentini DOC and the broader Chianti denomination; several good small producers are based in the surrounding hills. Check the town website for exact dates, which vary by year.