The “Festa del Vino” is the most important event in Montespertoli and one of the most recognisable highlights of the Tuscan wine calendar. For almost seventy years, it has celebrated the town’s identity through its most iconic product, reflecting the evolution of a community that has built its image, its economy and its pride on wine.

The origins: from the Cattle Fair to the birth of the “Festa del Vino”

The “Festa del Vino” has its roots in the traditional ‘Livestock Fair’, an event held on the third Wednesday before Easter to promote the significant livestock production of the Montespertoli area. In 1957, during the event held on 1 April in Piazza del Popolo, the idea took shape to pair livestock with another key local product: wine. A number of farms began to showcase their own labels, meeting with immediate approval.

From that enthusiasm, the following year saw the birth of the 1st Fine Wine Fair: just a few stalls, a large turnout, and the realisation that the wine from the hills between Florence and Siena deserved to be known and celebrated. The organisation was supported by several major local farms, which took part with floats decorated with wine flasks, and was soon entrusted to the Pro-Loco Committee. This is where the long history of the event begins.

Growth and a focus on promotion

From 1991 onwards, the event’s promotional role was strengthened, becoming a genuine tool for promoting Montespertoli and its products, both in Italy and abroad. The festival grew year on year until it reached a nine-day programme, featuring an ever-increasing number of farms, side exhibitions, shows, concerts, conferences, guided tastings, a funfair and cultural initiatives.

Over the decades, the event has also changed its name: for many years it was known as the “Mostra del Chianti”, until, on the occasion of the 68th edition, a new organising committee chose to restore it to its original name of “Festa del Vino”. A decision which, after so many years, marks both a return to its roots and a relaunch for the future, accompanied by a complete overhaul of the event’s image and brand.

Today, the Festa del Vino is a major cultural and entertainment event, capable of satisfying both wine connoisseurs from an oenological perspective and families and tourists seeking the flavours of Tuscan tradition over a good glass of Chianti.

The festival today

The “Festa del Vino” takes place every year from the last Saturday in May to the first Sunday in June, for a total of nine days, in Piazza del Popolo and Piazza Machiavelli, the heart of the town. At the stands of local wineries, visitors can taste the wine by purchasing the official “Festa del Vino” glass, which also becomes a small collector’s item each year.

Alongside the wineries, local associations ensure the event is also suitable for families and those seeking the flavours of traditional Tuscan cuisine. Exhibitions, shows, concerts, conferences and guided tasting tours organised by the event’s technical partners — Slow Food, Assoenologi, Viticoltori di Montespertoli, ANAG, FISAR, La Sciabola sul Collo and other industry associations — accompany visitors throughout the event, fostering a continuous dialogue between wine culture, gastronomy and social interaction.

The Contrade: the challenge that brings tradition to life

At the very heart of the event are the Contrade of Montespertoli. In recent years, thanks to the efforts of a large group of young locals, the “Torneo delle Contrade” has returned: the residents of Cappella, Fontanelle, Fornace, Mura and Pozzo compete in sporting events and challenges linked to agricultural tradition — mixed relay, wood-splitting, tug-of-war, hay bale rolling, cart race — culminating in the awards ceremony and the Contrade Evening. The trophy up for grabs is a precious ceramic flask depicting the five Contrade. The Gruppo Novecento parade.

The final day of the festival is dedicated to the historical re-enactment by the Gruppo Novecento, founded in 2007 to mark the event’s 50th anniversary. The procession, reconstructed with great historical accuracy, depicts the period between 1910 and 1930 and sets off from Sonnino Castle to reach Piazza del Popolo, accompanied by re-enactors, floats, animals and vintage cars.

The re-enactment, deeply rooted in the history of the area, has great cultural significance: every year it encourages local residents to take part as ‘re-enactors’, undertaking research and recreating period costumes and accessories. The procession features all the characters of early 20th-century rural society — from the “landlords” to the “sharecropper”, including the parish priest, the doctor and the mayor — interspersed with floats drawn by the imposing Maremmano and Chianina breeds, symbols of the area’s agricultural heritage.

A festival, a territory

Over almost seventy years of history, the “Festa del Vino” has become much more than a wine event: it is the living story of Montespertoli, its people and its landscape. A festival that spans generations, preserves rural heritage and projects into the future the identity of a territory that has found its most authentic voice in wine.