A friend and I are planning to go to Madrid and Lisbon for 10-11 days in October/November. If we take the train, can anyone recommend a good stop or two that might be nice for a night or two in between? Thanks.

We stopped in Caecares (sp?) which has a delightful, exzceptionally nice old town. Be sure to take in the local wine tastings if into vino.
Badajoz, Portugal is also nice - it has a famed aqueduct running a long way up to it. We stopped in both and enjoyed them very much.

My friend and I drove from Madrid to Lisbon. We stopped for lunch in Merida, Spain, and for dinner in Evora, Portugal, where the food was superb!

The Trenhotel runs between Madrid and Lisbon, departing Madrid at 22:45, arriving in Lisbon at 08:14. You can book the Trenhotel to Caceres (it arrives at 02:57)

There is a Regional that will take you to Plasencia, Caceres, Merida and Badajoz. The Talgo will take you to Caceres, Merida and Badajoz.

You can book the Trenhotel to Caceres (it arrives at 02:57 and departs at 03:00 for Lisbon), or take the Regional or Talgo, picking up the Trenhotel in Caceres for the trip into Lisbon.