October is one of the months I love most in Tuscany and Umbria. The light is softer, the hills glow in golden tones, and every weekend there’s a festival waiting to surprise you. From medieval pageantry to chestnuts roasting in the streets, saffron fairs and truffle hunts, this is the time when the region feels most alive — and most authentic.

Here’s my personal guide to the events you can enjoy this October 2025, listed by date so you can plan your t

🍁 Early October

October 2 to 5 – Eroica Bike Ride (Gaiole in Chianti, Tuscany)

This isn’t just a race; it’s a celebration of vintage cycling culture. Riders in retro jerseys take on the legendary strade bianche (white gravel roads), and the whole village becomes a festival. Even as a spectator, it’s a thrill.

October 3 to 5 – Corciano castello del Vino – a wine festival at the Corciano Castle.

3 days exploring the best Umbrian wines and events in a beautiful location.  Click here to buy the entrance ticket

October 4 – Feast of St. Francis (Assisi, Umbria)

There’s nowhere like Assisi on this day. The whole town gathers to celebrate Italy’s patron saint with processions, religious ceremonies, and a festive market atmosphere. You’ll feel the spirituality and community in every corner.

October 4–5 – Arezzo Antique Fair (Arezzo, Tuscany)

I adore wandering the antique stalls in Arezzo’s historic centre. The first weekend of the month transforms the piazzas into a treasure hunt of vintage finds, furniture, jewellery, and crafts. Even if you don’t buy, the atmosphere is worth the visit.

🍇 Mid October

October 10–11 – 12  – Borgo di Vino in Spello.

A wine festival in Spello.

October 10–19 – Chestnut Festival in Piegaro (Umbria)

I always say: if you want to taste autumn, go to Piegaro in mid-October. For ten days, the town celebrates chestnuts with roasted marroni, cakes, wine, music, artisan markets, and even special events at the glass museum. It feels like stepping back into village life.

October 10–19 – Autumn Festival in Abbadia San Salvatore (Mount Amiata, Tuscany)

The chestnuts here taste different — sweeter, richer, and roasted on huge open fires. Abbadia’s medieval centre fills with music, food stands, and autumn aromas. The mountain air adds to the magic.

October 12-19  – Mushrooms  Festival in Campiglia d’Orcia (Val d’Orcia, Tuscany)

Campiglia’s festival is small but full of heart: mushrooms, mulled wine, and panoramic views of the Val d’Orcia in autumn. A perfect Sunday trip.

October 12–20 – Fiera di San Luca (Impruneta, Tuscany)

A fair that has been going on for centuries! Originally a livestock fair, today it’s a lively mix of stalls, food, music, and traditions. The locals love it — and you’ll feel like part of the community.

October 10 to 12 and 17 to 19  – Beans Festival. A food festival all about local beans at Cave di Foligno 

October 13 to 15 and 20 to 22  – Sagra della Castagna (Arcidosso, Mount Amiata, Tuscany)

Arcidosso is chestnut heaven. With its medieval streets decorated for the festival, you’ll find chestnut-based dishes, artisan stalls, concerts, and tastings of the prized IGP chestnut of Amiata.

October 17–19 – Terre di Pisa Food & Wine Festival (Pisa, Tuscany)

This is Pisa at its most delicious. Wines, cheeses, olive oils, and traditional foods from the Pisa province take the stage. Go hungry — and ready to fill your suitcase with local specialties.

October 18 3.00 to 6.00 PM Il Fontanaro Grand Olive Mill Opening. Celebrate the new harvest with us at il Fontanaro.  To take part just email to info@countryslowliving.com

🌰 Late October

October 25–26  and 27 – Sagra del Tordo (Montalcino, Tuscany)

Medieval flags flying, archery competitions, and banquets with local game dishes — all in the heart of Brunello country. The combination of pageantry and wine is simply irresistible.

October 25 – Foligno “Umbria in a Glass” Wine Festival (Umbria)

Foligno opens its medieval centre to wineries and food stalls for a weekend of tastings. It’s vibrant, authentic, and less touristy than bigger events — which makes it extra special.

October 26 – Ottobre Trevano Finale (Trevi, Umbria)

The closing of a month-long celebration: the Palio dei Terzieri, medieval parades, taverns serving historic recipes, and the Black Celery market. If you love history and pageantry, this is the event.

October 26–27 + 1, 2 and 3 of November – VolterraGusto & White Truffle Fair (Volterra, Tuscany)

The season of white truffles begins here. Volterra’s medieval streets host tastings, markets, and truffle hunts. Pair it with local wines and artisan crafts for a perfect autumn weekend.

🎃 End of October

October 31 – Crastatone, Chestnut Festival (Piancastagnaio, Mount Amiata, Tuscany)

This is the oldest chestnut festival in the region, and you can feel its history. The whole town of Piancastagnaio smells of roasted chestnuts, and every alley hosts food stalls and music. A real mountain festa.

October 31 to November 2  – Città della Pieve Saffron Festival (Umbria)

This little town bursts with golden color, celebrating saffron with tastings, cooking demonstrations, and cultural events. I love how saffron finds its way into every dish.

October 31 + November 1, 2 and 3 the Truffle Fair in Gubbio 

October 31 – Halloween in Chianciano Terme (Tuscany)

Chianciano’s old town embraces Halloween with decorations, live music, and family-friendly activities. A fun way to end the month, Tuscan style.

Paciano 31 of October wit the English Studio for kids up to 10 years old

Chiusi Old Town at Terziere Sant’Angelo with wines for adults and sweet for kids

✨ Why October is Unmissable

October in Tuscany and Umbria is not about ticking boxes; it’s about living experiences. Eating roasted chestnuts in the shadow of a medieval tower, tasting peppery new olive oil straight from the press, or hearing the sound of drums during a Palio parade.

It’s the month when traditions are alive, food is at its best, and the crowds have gone. If you want to see Tuscany and Umbria at their most authentic, October is the time.