I've spent the last few weeks in Monterey, so it seems like I should have some more advice. Coast Weekly is the local free weekly paper that details all the upcoming events. Mainly it only deals with the upcoming week, but the plays and such have longer runs.

Defintly make a a day trip down to San Simeon. It's a fairly long drive, but doable if you spend the whole day. I suspect you'll enjoy it far more than the winchester mystery house, though I've never been.

Good Luck,
Matthew