Road trip in Portugal

I've been to Portugal twice, separated by many years, and the last time was way back in 2002 (where have the past 16 years gone?!?), but both trips included an overnight stay in Obidos. So my default place to stay between Lisboa and Porto, Obidos is about 50 miles north of Lisbon, and 100 miles south of Porto, not exactly halfway, but not way too far away from either. Coimbra is about 100 miles north of Lisboa and 50 miles south of Porto, so that's another option, but Obidos is a town and Coimbra's a good-sized city. It doesn't seem that you're trying to make plenty of time for your visit in and around Evora. Enjoy!
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I disagree with the previous poster regarding Obidos. While it may have been wonderful in 2002, today it is overrun by tourists. Lots of big bus tours and is not a lot of fun anymore.. I would vote for Coimbra, Tomar, or maybe Alcobaca. These towns aren’t so overrun and have a lot of history.
I know you wrote you like to travel fast, but Castelo do Rodrigo is way out of your way and there are many other castles to see. There is one outside of Tomar, that is pretty great. It’s Almourol and is best accessed by boat. It’s a beautiful setting and much easier to get to from your main route between Lisbon and Porto.
You can also take the train from Lisbon to Evora, possibly easier than driving.
And, coming October is much better than the summer, but still plan on a lot of tourists in the more popular areas.

I agree with Kathryn about Obidos. It’s worth a 2 hour visit if it’s not out of your way, but I visited in October 4 years ago and it was very busy.

If possible, it would make more sense to fly into Lisbon and back from Porto to avoid back tracking. All your stops are very rushed.

You don't need a night at Evora. Do the city on a day trip from Lisbon.

You can see the city easily in one day.

Regarding Obidoa, it would be a crime to miss that historical city. Yes, it has lots of tourist, so do most places that are great to visit.

The town was founded by the Romans and walls date back to them.
Consider going to Batila Cathedral on your way to Porto.

Don't forget going to Sintra, you can do that on a day trip from Lisbon.
Nazare is a great place you might consider for an overnight.

Thank you all for your replies! I really appreciate you taking the time to respond.

We are skipping Castelo Rodrigo and slowing down a bit. Thinking of adding a day to Lisbon and taking the train to Evora and back, then picking the car up.

Unfortunately we are flying round trip to Lisbon, instead of an open jaw with Porto, but we got an incredible fare out of SFO.

Any other suggestions of things we can't miss between Lisbon and Porto?

Thanks much!