Texas to Pittsburg...and beyond!

[chollas]

The long story short is, that a lady friend of mine wants to show me Pittsburg, where her sister lives. Thus the trip was born.

I have prior commitments until December 29 and then again on January 17. This trip does not have to span the entire time frame, but I am open to your suggestions. We will be departing from Austin. I enjoy culturally-unique cities and natural landscapes. I truly love local flavors more than a lot of things in this world so, for me, unique (or just plain tasty) food will be a large part of my planning. I would like to only stay in Pittsburg for a few days and then continue on the trip from there.

I have hopes to check out the Great Lakes and head into Canada as I have never been to its eastern parts. I have a friend in Toronto, so that will be a stop. Is it worth going deeper? Will the roads be too wintry?

I would also like to take different routes there and back. I am also open to going fairly far out of the way if it is worth it.

As you can see, this is something that is very open. I NEED your expertise as I have never road tripped out east, only several times West. I am open to suggestions and will help with any questions that you may have.

Thanks in advance for all your words!