October 2026 in Southern Tuscany and Northern Umbria
October 2026 in Southern Tuscany and Northern Umbria: The Month We Wait For
There is a particular sound to October here: chestnuts cracking over a fire, glasses touching in a village square, and, at our farm in Paciano, the first olives of the season tumbling into the mill. The light lingers on the hills, the tables get longer, and you no longer need a reason to stop for lunch.
I live between southern Tuscany and northern Umbria, and this is the month I tell friends to come. Some weekends ask you to choose between three festas; others are best left open for a walk, a glass of wine and whatever is cooking in the piazza. Here are the October 2026 dates I would put in my diary. Follow the full links for programmes, tickets and any last-minute changes.
The first weekend: vintage bicycles, wine and old treasures
October 2–4 | Corciano Castello di Vino, Umbria. Corciano turns its stone lanes and old ground-floor rooms into a wine trail. It is a lovely way to meet Umbrian producers while wandering one of our prettiest little towns. The event also helps fund restoration of the village’s historic heritage. Programme and tickets: https://www.
October 2–4 | Festa dell’Uva, Cinigiano. The Maremma has its own harvest rhythm. In Cinigiano, open cellars, local wines, music and the colourful allegorical float turn a village weekend into a celebration of the grape. Organiser: https://www.prolococinigiano.
October 3–4 | L’Eroica, Gaiole in Chianti, Tuscany. Wool jerseys, old steel bicycles and white roads: even from the roadside, L’Eroica is a wonderful spectacle. If you are driving through Chianti that weekend, allow extra time and let the cyclists set the pace. Official event: https://www.eroica.cc/eventi/
October 3–4 | Arezzo Antiques Fair. Start in Piazza Grande, then let the stalls lead you down the side streets. I always find the objects with a story more interesting than the ones with a perfect polish. Official calendar: https://fieraantiquaria.org/
October 4 | St Francis Day in Assisi. This is a day to experience Assisi with patience and respect for its religious celebrations. Check the local programme before you travel: https://www.comune.assisi.pg.
October 2–25 | Ottobre Trevano, Trevi. Trevi spends much of October reliving its medieval traditions. The Palio dei Terzieri falls on October 4; on October 17–18, look for the Black Celery market and the sagra of sedano nero and sausage. The taverns and processions make a return visit worthwhile. Official programme: https://www.ottobretrevano.it/
October 9–18: the first real taste of autumn
October 8–11 | Boccaccesca, Certaldo Alto. A food and wine festival in the upper town of Certaldo, where the lanes themselves make you want to linger. This year’s theme brings Pinocchio into the story. Municipality listing: https://comune.certaldo.fi.it/
October 9–11 | Borgo diVino, Spello. Wine tastes especially good in Spello’s flower-framed lanes. Go for a glass of Grechetto or Trebbiano Spoletino, and stay to talk to the people who made it. Official information: https://borgodivino.it/spello/
October 9–11 and 17–18 | Pietralunga White Truffle and Potato Market. If you want to meet the people behind the flavour, go north to Pietralunga. The town celebrates both the white truffle and its local potatoes, with producers and cooking events across two weekends. Destination programme: https://visitpietralunga.it/
October 9–18 | Piegaro Chestnut Festival. This one is close to home. Follow the scent of roasted chestnuts into Piegaro’s historic centre, then linger over the local dishes and small-town atmosphere. Regional event page: https://www.umbriatourism.it/
October 9–18 | Sagra del Fagiolo di Cave, near Foligno. Cave celebrates its local beans across two weekends. It is the sort of village meal that makes you wonder why you ever rushed lunch. Regional calendar: https://www.umbriatourism.it/
October 10–18 | Festa d’Autunno, Abbadia San Salvatore. On Mount Amiata, autumn has its own kitchen: mushrooms, chestnuts, castagnaccio and recipes made for cooler air. The medieval quarter is part of the pleasure. Organiser: https://prolocoabbadia.it/
October 10–18 | Fiera di San Luca, Impruneta. A historic fair with deep roots in Tuscan rural life, and a good excuse to explore the town’s terracotta tradition. Official destination listing: https://www.feelflorence.it/
October 11 | The first olives go into our mill at Il Fontanaro, Paciano. This is the day we plan to begin pressing our 2026 harvest. Fresh oil straight from the mill is green, fragrant and lively, and I still think the best way to meet it is on warm bread. Harvest timing depends on the olives and the weather, so follow us for updates . Our farm and stays: https://www.countryslowliving.
October 17–November 15 | Frantoi Aperti in Umbria. Across the region, olive mills open their doors during the new-oil season. Each weekend offers a different reason to follow the olive groves: a tasting, a village walk, or the sight of oil emerging from the press. Regional calendar: https://www.umbriatourism.it/
October 17 | Come taste the new oil with us at the Fontanaro olive mill. The following Saturday, we are planning a small gathering for friends in Paciano to celebrate the new harvest. Come see the mill and taste the first oil with us. For the precise time, directions and to let us know you are coming, email info@countryslowliving.com. We will share the final details closer to the day at https://www.instagram.com/
Mid-month: follow the mountain roads
October 11 and 18 | Sagra del Fungo e della Castagna, Vivo d’Orcia. A mountain-village outing for mushroom and chestnut lovers. Confirm the day’s programme before setting off: https://www.prolocovivo.org/
October 16–18 | Terre di Pisa Food & Wine Festival. If your October travels take you farther west, Piazza Vittorio Emanuele II becomes a showcase for the producers and flavours of the Pisa area. Official festival: https://
October 17–18 and 24–25 | Caprese Michelangelo Chestnut and DOP Marrone Festival. A celebration of the prized local chestnut among the woods of the Tuscan Apennines. The trip is best enjoyed slowly, with time for both the village and the mountain views. Local destination information: https://www.meetvaltiberina.
October 16–25 | La Castagna in Festa, Arcidosso. Arcidosso’s old streets and cellars belong to the chestnut for two October weekends. This is a good day to combine the festa with a drive through the woods of Mount Amiata. Local listing: https://toscana.piazzainfesta.
The last weekends: archers, truffles and saffron
October 23–25 | Sagra del Tordo, Montalcino. The four neighbourhoods bring their colours, kitchens and archers into the streets. Go for the procession and stay for the communal tables; the Sunday archery contest is the climax. Official programme: https://sagradeltordo.it/en/
October 24–25 and October 31–November 1 | VolterraGusto. White truffles, local produce, tastings and the singular drama of Volterra’s medieval streets. It is farther from Paciano, but makes a fine overnight trip. Official event: https://www.volterragusto.com/
October 30–November 1 | Festa del Bosco, Montone. Montone’s lanes fill with the produce of the woods for the 42nd edition of this autumn celebration. It is a lovely choice for anyone who wants a village day built around chestnuts, mushrooms, small producers and the changing colours of northern Umbria. Municipality listing: https://comune.montone.pg.it/
October 31–November 1, November 7–8 and 14–15 | Città di Castello White Truffle Fair. Three weekends devoted to the white truffle of the Upper Tiber Valley. Regional programme: https://www.umbriatourism.it/
October 30–November 1 | Crastatone, Piancastagnaio. At the turn of the month, follow the scent of crastate (roasted chestnuts) through the old town. Confirm the full 2026 programme with the organisers: https://www.
October 30–31 and November 1, 6–8 | Gubbio White Truffle Market. Gubbio is especially atmospheric in late autumn. The 2026 market is scheduled in Piazza Quaranta Martiri across these two sets of dates. Municipality announcement: https://www.comune.gubbio.pg.
Late October | Zafferiamo, Città della Pieve. Saffron is one of the treasures of the town next door to us, and its autumn celebration is worth watching. As of September 28, the 2026 dates shown by independent listings disagree, while the consortium’s event page still describes the 2025 edition. I will add the exact 2026 dates as soon as the organiser announces them. Organiser updates: https://www.
A date to save for November
If you have seen an Instagram calendar placing Eurochocolate in October, note the change: the organiser lists November 13–22, 2026 in Perugia. Official dates: https://www.eurochocolate.com/
Make an October weekend your own
My favourite plan is simple: choose one festa, leave space for an unplanned village, and keep a piece of bread ready for the new olive oil. From our home in Paciano, you can make easy days around Lake Trasimeno, Città della Pieve, Montepulciano and Mount Amiata, then return when the hills turn violet in the evening.
By Alina, Il Fontanaro, Paciano. Event programmes can change; check each organiser’s full link before travelling. Last checked September 28, 2026.
