I second the recommendation for Monticello; it is very interesting. Michie Tavern is very near there. Montpellier is a little distance away. I haven't been in awhile.
On the weekends, the downtown walking mall is pretty active. There are a number of restaurants down there. there are some neat looking shops there also. The Barracks Road shopping center has a number of upscale shops along the lines of Anthropolgie, etc.
I had a lunch at the Main Street Grill; chicken sandwich with spinach/artichoke dip that was awesome. I also ate at an Italian restaurant outside on the mall, but I can't remember the name of it for the life of me.
I really like Charlottesville. Have fun.