Maybe I'm just missing it or maybe there's no such setting in Cakewalk.
 
Is there a setting that will make it so that when I hit Stop, either when in playback or recording, the playhead will automatically return either to the 1:00:00 point or to the place where I started playback/recording?

Options-->On Stop Rewind to Now Marker

Sure, in the option menu in track view. That is how I have always had things set. 
 
On stop, rewind to now marker.........

W is return to zero 
CTRL+Spacebar on stop rewind to now
Spacebar stop
CTRL+W and Track View On Stop, Rewind to Now menu option swap CTRL+Spacebar and Spacebar

Thanks! I knew it had to be there somewhere.

That Ctrl W toggle is something I use a lot. 

Man, this forum is wonderfully top-heavy with knowledge.
 
2 accurate and helpful replies, 1 exhaustive reply, my thanks, and a follow-up useful reply, all within about 15 minutes!
 
Once new users can register, it's going to be fun to watch you all work on a daily batch of newbie questions like this, and I know I'm going to learn a lot.