The Fiera di San Luca, held over two weeks in mid-October around the feast of Saint Luke (18 October), is one of the oldest fairs in Tuscany — first documented in 1473 but already an established tradition by then. It began as a livestock market that brought farmers and herders down from the surrounding hills and grew into a full agricultural festival. The fair takes over Piazza Buondelmonti and the surrounding streets with stalls, food, music, and a small funfair.
Modern Fiera mixes serious business with party. There are livestock judging, terracotta competitions, tastings of Chianti wine, olive oil, and the chestnut-flour castagnaccio that comes into season here, plus fireworks on the closing weekend. Local families come down from Florence to eat bistecca alla fiorentina and tortelli di patate at long communal tables. Worth timing a Tuscany trip around if you happen to be in the area in October.