The medieval village transforms into an open-air museum where great masterpieces of painting come to life.
The Living Paintings of Montemassi are one of the most evocative cultural events in the province of Grosseto. Every year, between late May and early June, the medieval village of Montemassi, a hamlet of Roccastrada in the heart of the Tuscan Maremma, transforms into a grand open-air art gallery. Masterpieces from the history of painting are recreated live by flesh-and-blood performers, perfectly posed and motionless, within sets that faithfully replicate the original works.
The exhibition is a traveling route through the streets, squares, and panoramic viewpoints of the historic center. Visitors are guided in small groups with staggered departures, allowing them to admire each scene at a leisurely pace and be surprised by one painting after another. The meeting point and departure is the charming Piazza della Madonna, where the event kicks off in the late afternoon.
Each edition proposes a selection of works inspired by a different theme: from the great masters of the Renaissance to contemporary artists, from classic portraits to more dreamlike and surreal visions. The scenes include works by famous painters such as Botticelli, Leonardo da Vinci, Monet, Chagall, Picasso, and Salvador Dalรญ, alongside more surprising authors less known to the general public.
Behind every edition lies months of work by over one hundred people: performers, costume designers, makeup artists, hairdressers, carpenters, builders, electricians, set designers, and figurative art enthusiasts. The organization is managed by the Circolo Arci of Montemassi, with the patronage of the Municipality of Roccastrada. It is an event deeply rooted in the community, capable of involving residents of all ages and transforming an entire village into a collective work of art.
Along the route, the visual experience is accompanied by live music and moments of hospitality that highlight the Maremma spirit. The exhibition attracts hundreds, and in some editions over a thousand, visitors every year, becoming a highly anticipated appointment not only for the inhabitants of Roccastrada but for all of Tuscany.
Visiting the Living Paintings is also the perfect opportunity to discover Montemassi, dominated by the remains of its medieval castle, made famous by the fresco by Simone Martini preserved in the Palazzo Pubblico of Siena. Between nature, history, and art, the event offers an unforgettable journey into the tradition and creativity of the Grosseto Maremma, in Tuscany.
The thirteenth edition of the Living Paintings of Montemassi was held on Sunday, May 31, 2026, with the theme "Art plays with me. Extravagances. Oddities. Dream and reality." The village, a hamlet of the Municipality of Roccastrada (Grosseto), once again transformed into an open-air museum.
Sixteen paintings by famous artists were reproduced live, including Michael Cheval, Marc Chagall, Salvador Dalรญ, and Vincenzo Caprili; the opening work was "Saint Catherine of Siena negotiating with Pope Gregory XI" by Eleanor Fortescue. The presentation was entrusted to Marcello Pagliai. Over one hundred volunteers worked for months on the creation of the scenes.
4:00 PM โ presentation in Piazza della Madonna by Marcello Pagliai, followed by group departures along the route in the village. Last departure at 6:00 PM. Sixteen paintings on display, accompanied by music from the San Martino Choir of Roccatederighi.
Montemassi is a hamlet of the Municipality of Roccastrada (GR), in Tuscany. By car, it can be reached via the SS73 or the SP road to Roccastrada; it is about 30 km from Grosseto. The nearest train station is Montepescali-Roccastrada, on the Tirrenica line.
Admission to the event is free. Along the route, there are refreshment points and stations to support the initiative. Departures take place in groups in the late afternoon, starting from Piazza della Madonna.
We recommend wearing comfortable shoes for the route along the cobbled streets of the village and arriving early to witness the initial presentation.
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Borgo di Montemassi
Piazza della Madonna, 58020 Montemassi