🍂 Early November (November 1–5)

Fiera dei Morti – Perugia (to be confirmed)

One of Italy’s oldest fairs, dating back to the Middle Ages, the “Fair of the Dead” fills Perugia with hundreds of market stalls offering local crafts, food, and curiosities. It usually takes place from November 1 to 5.

Official info: https://www.comune.perugia.it/

Vaiano – Madrevite Winery 

enjoy sunset views in the vineyard with music and local street food. From 3 to 8 PM.

Piancastagnaio – Il Crastatone (Chestnut Festival) up to November 2

On the slopes of Monte Amiata, this charming festival celebrates chestnut season with roasted chestnuts, red wine, music, and medieval pageantry. It typically runs the first weekend of November.

Official info: https://www.comune.piancastagnaio.si.it/

Arezzo Antique Fair

One of Italy’s most iconic antique markets, the Arezzo Fiera Antiquaria takes place every first weekend of the month — this year, November 1–2, 2025. The historic center becomes a collector’s dream of vintage furniture, jewelry, and ceramics.

Official site: https://www.fieraantiquariaarezzo.it/

Gubbio – 31 Oct to 2 of Nov and 8 and 9 of November

The White Truffle Market Fair celebrates not only the excellence of the local truffle, but also the finest agricultural and food products: pasture-raised cheeses, cured pork products, select meats, olive oil, honey, and traditional sweets. This truly remarkable event is held in the heart of the historic center, amidst squares and buildings that evoke the pristine atmosphere of the medieval city.

🥖 🌿 Second  and Mid Weekend (around November 7–17)

Wine & Chestnut Festival – San Martino in Colle – November 7–16, 2025

San Martino in Colle (Perugia, Umbria) – Celebrate autumn in Umbria at the 47th edition of the Wine & Chestnut Festival in San Martino in Colle. This beloved local tradition brings the community together to enjoy the season’s most authentic flavors — from fragrant roasted chestnuts to excellent local wines and a wide selection of regional specialties.

Don’t miss the famous torta al testo, a traditional Umbrian flatbread, along with many other delicious dishes prepared with local ingredients.

Anghiari – Festa di San Martino e dei Bringoli November 15 and 16 

Held the second weekend of November, this warm, down-to-earth celebration honors San Martino with handmade “bringoli” pasta, chestnuts, and mushrooms — perfect for a cozy Sunday lunch in Tuscany.

Official info: https://www.comune.anghiari.ar.it/

🌿 San Giovanni d’Asso – White Truffle Festival 8/9 and 15 and 16 of November

A small, authentic truffle fair in the Siena countryside with tastings of truffles, pecorino, and the new olive oil.

Eurochocolate – Perugia

Italy’s most famous chocolate festival returns November 14–23, 2025, taking over Perugia’s historic center with tastings, workshops, installations, and a “bean to bar” journey.

Official site: https://www.eurochocolate.com/
Tourism info: https://www.umbriatourism.it/en/-/eurochocolate-event

While you’re nearby, plan a peaceful afternoon in Assisi — you can read my post here: https://www.tuscanyumbriablog.com/assisi/

San Miniato – White Truffle Fair (First Weekend)

The 54th National White Truffle Fair of San Miniato opens its first weekend November 15–16, 2025, transforming the medieval town into a gourmet paradise with cooking shows, truffle hunts, and wine pairings.

Official info: https://www.sanminiatopromozione.it/
Visit: https://www.visitsanminiato.com/01_ita-mostra-mercato-del-tartufo-bianco-di-san-miniato-festa-sagra-degustazione-piatti.html

Frantoi Aperti – Open Olive Mills (across Umbria)

All month, olive mills open for tastings, tours, music, and village events celebrating the olio nuovo. Nothing captures Umbrian culture better than dipping fresh bread into the season’s first press.

Official site: https://www.frantoiaperti.net/

Vintage exhibition – Bastia Umbra

At Umbriafiere, this fair celebrates vintage  living, reuse fashion, and old times — a great alternative day trip if you’re near Perugia.

Venue: https://www.umbriafiere.it/

🍷 Late November (November 18–30)

Acquasparta – Festa del Vino Novello e dei Prodotti Tipici (to be confirmed)

This traditional festival celebrates the arrival of vino novello with local food tastings and music in the medieval streets of Acquasparta, typically around mid to late November.

Official info: https://www.comune.acquasparta.tr.it/

Spello – Festa dell’Olio e Sagra della Bruschetta (to be confirmed)

Usually the last weekend of November, this joyful celebration honors the new olive oil with tastings, open mills, and music. Spello’s golden stone streets glow beautifully at this time of year.

Official info: https://www.comune.spello.pg.it/

San Miniato – White Truffle Fair (Final Weekends)

The truffle fair continues on November 22–23 and 29–30, 2025, making San Miniato a must-visit destination for food lovers all month long.

Event page: https://www.terredipisa.it/events/mostra-mercato-nazionale-del-tartufo-bianco-san-miniato/

Gubbio – White Truffle Festival (to be confirmed)

Usually spread across multiple weekends in November, Gubbio’s truffle fair blends gastronomy and craftsmanship in one of Umbria’s most atmospheric medieval towns.

Official info: https://www.comune.gubbio.pg.it/

✨ My Dream November Itinerary

• Early November: antique hunting in Arezzo and roasted chestnuts in Piancastagnaio.
• Mid-November: truffles in San Miniato and chocolate in Perugia (plus a peaceful afternoon in Assisi).
• Late November: olive oil tastings in Spello and Frantoi Aperti visits across Umbria.

Note: Events marked “to be confirmed” typically announce final dates closer to the month. Always check the official links before you go.