Hi Karen --
Another suggestion for a day trip from Madrid. We were in Sigüenza today, the province of Guadalajara. It's a beautiful town with an impressive cathedral and castle. While it isn't quite Toledo, it is historical in its own right and very medieval. You certainly won't run into the tourist crowds that you will in Toledo. The train station is right in the middle of town as well... it is on the Madrid-Barcelona line.
I haven't put our pictures up on a website yet, but found
this webpage that has some great shots.
On Sunday we will be heading to
Cuenca to see the Casas Colgadas (I've seen them before but my husband, who is Spanish, hasn't!) among other things.
Hopefully your notebook of ideas is getting full!