Check out Driftless Trout Anglers
for some info. I just started fishing the drifltess area this summer, and have learned quite a bit from this site, and from my experiences on the stream.
I like streams in Grant County, but thats because its an hour closer to me than Viroquoa is, although I plan on taking a week off to trout fish in the summer, and I'll be checking that area out for sure. As for the right times to fish, I can't really help you out there, I just try and get up there whenever I can haha.
Have fun up there next year, let me know if you have any questions.
Edit: I noticed you said you were from the Racine area, how's the Root River fishing. I plan on taking a trip up there on Thursday after finals are over for my first steelhead/lake run brown fishing experience, what can I expect?