Goblets under the Castle
Wine, local flavors, and live music in the village of Montemassi
About Goblets under the Castle
Goblets under the Castle: Maremma wine beneath the fortress of Montemassi
In the heart of the Tuscan Maremma, the medieval village of Montemassi — a hamlet of Roccastrada, in the province of Grosseto — hosts Goblets under the Castle every summer, a food and wine event dedicated to local wines. For one evening, the streets and squares of the historic center come alive with stalls from local wineries, creating a sprawling tasting route that winds its way in the shadow of the fortress overlooking the town.
How the tasting works
At the entrance to the route, you can purchase a glass goblet accompanied by tasting coupons: with this, you can roam freely between the winery stations, toasting to the wines of the Maremma and the Monteregio district. The tastings are set up along the most characteristic streets and squares of the village — including Via del Capezzuolo, Piazza Salotto, Piazza della Chiesa, and Piazza Padella — accompanied by food stalls featuring local products and live music in several spots throughout the town.
An event created to showcase the territory
Goblets under the Castle is organized by the ARCI Montemassi association together with the Municipal Administration of Roccastrada and the Monteregio di Massa Marittima Wine and Flavors Route. The goal is to highlight the oenological vocation of this part of the Maremma, where wine has become one of the specialties of the Roccastrada area and where numerous companies, both small and large, preserve a tradition tied to the land and those who work it.
Montemassi and its castle
The backdrop to the event is the Castle of Montemassi, an ancient fortress that towers over the village and entered art history thanks to the fresco by Simone Martini depicting Guidoricchio da Fogliano, preserved in the Palazzo Pubblico of Siena. Walking through the narrow streets of the town with a glass in hand, under the castle walls on a typical summer night in the Maremma, is what makes this event particularly beloved by residents and visitors alike.
Who it is for
- Wine lovers and wine tourists discovering the wineries of the Maremma
- Families and groups of friends looking for a summer evening in a village
- Tourists staying between Grosseto, Massa Marittima, and the Maremma coast
- Those who love combining tastings, local products, and live music
Goblets under the Castle — edition 2026
Goblets under the Castle 2026 in Montemassi
The fourth edition of Goblets under the Castle is expected on Thursday, July 9, 2026, in the historic center of Montemassi, a hamlet of the Municipality of Roccastrada (Province of Grosseto). As per tradition, the medieval village transforms into a sprawling tasting route at the foot of the fortress, with stalls from local wineries set up between the streets and squares of the town.
By purchasing the glass goblet with tasting coupons, visitors will be able to discover the wines of the Maremma and the Monteregio district, accompanied by food stalls with local products and live music in the streets of the historic center. The event is organized by ARCI Montemassi together with the Municipal Administration of Roccastrada and the Monteregio di Massa Marittima Wine and Flavors Route.
The complete list of participating wineries, detailed schedules, and the musical program for the 2026 edition will be announced in the weeks leading up to the event on the Municipality of Roccastrada website and the organizers' channels.
Programme Goblets under the Castle 2026
The detailed program for the 2026 edition (list of participating wineries, station times, and musical proposals) has not yet been published and will be announced in the weeks leading up to the event.
Based on previous editions, the evening includes:
- Opening of the tasting route in the historic center of Montemassi in the evening
- Stalls of local wineries set up between the streets and squares of the village (in previous editions Via del Capezzuolo, Piazza Salotto, Piazza della Chiesa, and Piazza Padella)
- Food stalls with local products and refreshment points managed by ARCI Montemassi
- Live music in several spots throughout the town
Highlights Goblets under the Castle 2026
- Fourth edition of the village wine event
- Traveling tasting of wines from Maremma wineries beneath the castle of Montemassi
- A journey through wine, local products, and live music in the historic center
Prices Goblets under the Castle 2026
Practical information — Goblets under the Castle
How to get there
Montemassi is a hamlet of the Municipality of Roccastrada, in the province of Grosseto. By car, it can be reached from the SS73 and the provincial roads of the Maremma; the reference train station is Roccastrada (Grosseto-Siena line), from which you continue by car. The event takes place in the historic center of the village.
Tickets and tastings
Entrance to the village streets is free. To participate in the tasting route, you purchase the glass goblet with coupons for tastings (10 euros in recent editions). Food stalls are paid separately.
Tips
The event takes place in the evening: wear comfortable shoes for walking through the alleys and squares. Check the updated date and times on the Municipality of Roccastrada website before leaving.
Information
Roccastrada Info Point: [email protected] — Tel. +39 0564 561287. Organization ARCI Montemassi: +39 371 6925467.
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Where does it take place — Goblets under the Castle
Centro storico di Montemassi
Centro storico di Montemassi, 58027 Montemassi