If you had to choose two favorite spots in Puglia in October--what would they be?
We love ruins, and history and natural beauty (with hiking). And of course great food and old towns. My husband hates lying on the beach (and perhaps not beach season so that solves that)

Unfortunately we don't have a lot of time so I decided to limit to two places and just slow down and enjoy.
Thank you

Lecce old town is magnificent, the Roman ruins right in town, the quirky ways of the people.

Gravina is surrounded on 3 sides by a ravine that holds cave churches.

We didn’t see all the towns but we loved Lecce, too, and enjoyed Polignano a Mare as well. We visited several other towns but stayed in these 2 and found they complemented each other very well.

Yo RT, Puglia seems a tough place to choose just two spots from. The default fave in guidebooks and among many travelers, is Lecce. Great place and one of the largest in the area. Locorotondo might fit the bill for all of your above stated requirements. It also has a massive weekly market. Monopoli is much the most 'authentic local' of the various places there (chi chi Ostuni might represent the opposite of that 'residential' feel). Gallipoli is great but very contained and farthest away down in its southern location. The port Trani is way up at the top, and it too has its charms. Bari is a full-on city.

Our TR here 'Bella Puglia' might be of some use (no fotos yet). We were there in October 2017.
I am done. The end.

We just spent 17 days in Puglia but we have been there in October too. Last time we stayed in a Masseria in the Itria valley near Ostuni for part of our trip and that was fabulous and it was still warm enough to swim in their pool. You can do day trips and explore the area. Masseria Cervarolo.
Lecce is a beautiful little city, an easy place to just relax. I enjoyed Otranto this time more because being June it was a little more lively but for October I think the seaside towns in the very south of Puglia can be a little too quiet.

We discovered a new town this time which is now our favourite but I’m keeping it to myself.