Was just in the Charlottesville area, including Wintergreen, and offer the following: 1) If you go to Monticello -- for lunch, drive farther down the road for several miles to a place in what appears to be an old gas station -- across from a country church. (This place is basically in the countryside, with nothing other than this old gas station and the church in sight, so you won't miss it). This place had great sandwiches, made with a great homemade flat bread sort of like ciabatta, creative salads, a great asparagus soup, all of which you can carry out to the chairs outside at the front of the building. (There are no tables inside -- it's more like a deli counter & shop.) Outstanding!
Other posts have mentioned the Blue Ridge Pig, on the road to Wintergreen, in Nelly's Ford. An interesting note: I took my crew there to experience some VA bbq, even though I'm a veggie-head myself. Much to my surprise, the grocery right next door had a deli counter that made the best vegetarian BLT I've ever had, plus a good selection of side salads. Lots of vegetarian options. I just carried it over to the Blue Ridge Pig and joined my bbq pals.
In Charlottesville, I was amazed reading the basket of menus at the B&B where I stayed. This town out-California's California in terms of creative, fusion-y efforts. At Mono Loco, featuring Cuban and Spanish-inspired dishes, we all had wonderfully creative dishes, from paella to tamales to Bananas Castro, a slightly wackier version of Bananas Foster. Our waiter, who could compete credibly in any body piercing contest, was great and a perfect representative of this twisted-but-slightly-upscale place.