Ah - restaurants I can't help with much but a MUST VISIT - King Family Winery
We had some time to spare as we drove in to visit DH cousin who teaches at UofV. So we started following the signs for the Virginia Wine Trail and this was the first one we hit. The wines were nice but this was just an incredible place. They have this huge estate with horses and polo grounds. Locals bring their picnic baskets and come out for the day - it's a destination place even for locals. I think they also have some nice cheeses you can have with your wines also. But it's very scenic.
That night we ate at a restaurant - a brew pub down in the heart of old Charlottsville near the University and some railroad tracks. It was good but nothing special so you can probably find something better.