What to do in Cortona in October and surroundings (2019)

If you plan on visiting Cortona, Italy in October think about a slow vacation – regenerating morning walks, Tuscan food, and day trips!

Life in Cortona is slowly going back to the Winter months’ tranquillity. All the great exhibitions have come to an end. (Next on the agenda is Cortona On the Move’s 10th edition next year!) The good news is that this month you can enjoy brisk mornings, including sometimes the amazing show of the foggy landscape, and warm afternoons. Perfect to explore the surroundings and take a walk on the hills around Cortona. (Have you tried the walk to Bramasole yet?)

The second good news is that October brings plenty of delicious Autumnal produce and the best of Tuscan cuisine. Try porcini mushrooms, crostini with cavolo nero (kale), bruschetta drizzled with spicy, freshly squeezed extra-virgin olive oil, slow-cooked wild boar, chestnuts, and new wine.

What to do in Cortona in October: events and festivals

Some events are still on the calendar in Cortona. On Sunday, October 6 expect to see people dressed in medieval costumes holding crossbows and walking around in groups. There is the crossbows tournament in Piazza Signorelli (from 10 am to 6 pm), with archers coming from all over Italy.

On Friday October 11, the concert by the Italian singer Ginevra di Marco will take place in Fortezza del Girifalco. Also, on Sunday 13, a day of live musicals is on the calendar, all inside the “Cannoniera” (underground rampart) of the Fortress.

The next weekend (11-12-13), if you feel like taking a trip and living an “all-locals” adventure, there is the Chestnut Festival in Pierle. Pierle is a small village of twenty houses (just guessing!), in the mountains above Cortona, 20 minutes drive. The village is dominated by a medieval, almost-ruined castle and tower dating back to 1200 (read more here). You can have dinner there and enjoy roasted chestnuts around a bonfire.

On Sunday, October 13 another very interesting event is happening close to Cortona: Festa del Carro Agricolo in Fratticciola (website and images here). The festival celebrating the cart and the old agricultural society means a whole village showcasing their old tools, animals, and decorated carts on a lively Sunday. See the parade from 3.30 pm and don’t miss their genuine homemade food! Fratticciola is 10 minutes drive from Cortona in the countryside, with a beautiful view of the town from the distance.

Other events:

Antiques Fair in Arezzo – October 5 and 6
Polenta Festival in Rigutino – October 4 to 6 and 11 to 13
International Street Food Festival in Arezzo – October 11 to 13

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