Dolomites

Best to check websites that collect historic weather data. Although no one can predict exact weather conditions more than a few days out. Here's one site that gives weather averages for Cortona. You can change the location to the place you will be staying at

https://weatherspark.com/y/69014/Average-Weather-in-Cortona-Italy-Year-Round

In fall of 2024, there was unusual heavy snow mid September and then when I was there first week in October, there was some sleet and light snow on the trails. I only did easy hikes and had no problem with the light snow which made for lovely scenery. Appropriate layers of clothing are important. My hands definitely needed the light gloves I brought. A number of the lifts will be closed or closing while you are there. Check here.

The regional website with lots of info. It also leads to local weather and transport apps.

https://www.suedtirol.info/en/en
and
https://www.suedtirol.info/en/en/seasons/autumn

from the site:
"As soon as the vine leaves turn golden yellow and the grapes have been harvested, the Törggelen season begins in South Tyrol. The term stems from the ‘Torggl’, a wooden wine press found in farmers’ cellars. The name derives from the Latin word ‘torquere’, meaning ‘to twist’. From early October to late November, following the harvest, local taverns and farm inns open their parlours. Here, in a convivial atmosphere, you can sample South Tyrolean specialities such as homemade Schlutzkrapfen, Knödel dumplings, cured meat and homemade sausages with sauerkraut, sweet Krapfen doughnuts and roasted chestnuts. This is traditionally served with ‘Siaße’ (grape must) and young wine."

For trekking check out Gillian Price's hiking guides to the Dolomites.

The great thing about the Dolomites is that you can go up one lift, trek and go down another. The free bus pass your hotel will give you can get you back from wherever you come down. BUT, as noted many lifts will be closed for maintenance to get ready for the ski season.

Keep an eye on the weather:
https://weather.com/it/south-tyrol/city/urtijei/tenday

The lifts start closing down for shoulder season maintenance at the end of September. You might check the area you want to visit for their closure dates. Of course, you can always hike up like we did in the Alpe di Siusi but it was a bit of a straight hike up from the meadow. Much more enjoyable to take a lift up!

As others have mentioned, one never knows. We’ve been in the Val Gardena and Alpe di Siusi for great October weather and snow in September (that famous 2024 event mentioned above). Bring long underwear, sturdy shoes, gloves, warm coat, hat and be ready for anything with your layers. We’ll be there too, Oct 4-17 and plan to do lots of hikes. FYI, the last day for some of the lifts in Ortisei is Oct 11.