The village is situated on top of a hill between the Val di Chiana and Val d'Orcia. The first news on the population of the area date back to the men of Neanderthal (60,000 years ago) with the Lithic tools found in the area of "Il Tondo" (now the public garden). The territory also preserves traces of frequentation of Etruscan and Roman times. The village developed between the XII and the XIII century, first with the foundation of the church Pieve di San Leonardo by the cistercian monks of the nearby monastery, then as a fortified village of the Sienese Republic. The name derives from the latin fullones (people who worked the woolen clothes), this is because the monks dedicated themselves to fulling wool. Its strategic location, it was in fact a useful outpost against Montepulciano, ally of Florence. In 1543 surrendered to the imperial army of Charles V and became part of the Fiorentino dominion of doctors.
Montefollonico is surrounded by walls, which still preserve some cylindrical towers and tower of Cassero, 1277. You also retain the three gates (Porta in Follonica, gate of Triano and port of Pianello), which still give access to the historic center. The village houses the church of San Leonardo, remembered from 1216, the monastery of Santa Maria, founded by the benedictines before 1170 and abandoned in the XVIII century and the Palazzo Pretorio. The public cistern of Montefollonico is located next to the Palace of Justice in the main street. On the front of the well it can be noted that the three ancient coats of arms of relevance to the community of the country: the first belongs to the family of the marchesi Coppoli, according to the family Landucci and more in general to the Municipality of Montefollonico, the third represents instead a religious Corporation. The Natural Park The Tondo, near the village, at the top of the hill, consists in a wood of cypresses and holm oaks arranged in a circular fashion. Depart from here a series of walking paths around the hill.
The pecorino from the area, called a great old man of Montefollonico has a great reputation and recognition of P.A.T. "...it would like a dash of Vin Santo?..", instead, is the gastronomic fair held in December, focused on vin santo.