Charlottesville recs:
1)The most popular sandwich place in town is Bodo's bagels. It has multiple locations, including one right across the street from Mr. Jefferson's Rotunda, and serves bagels at least as good as NY Bagel & Bialy, though in a somewhat different style. Bellair Market is more gourmet and more expensive, though not necessarily better. Depends on your mood. Take it Away on Elliewood Ave. near the Rotunda/"Corner" also makes a nice sandwich for picnics on the Lawn or in one of the Pavilion Gardens.
2)Best pizza place in town is a few minutes outside town further down the same road as Bellair Market--Crozet Pizza. Good place with lots of local flavor, but not outstanding by Chicago standards. Good, though, and a good place to go after sightseeing on the Blue Ridge Parkway. Sylvia's Pizza on the downtown pedestrian mall (and elsewhere) used to be outstanding, but went downhill after the original owner sold it a few years ago. May be worth checking out.
3)A good "shabby chic" type restaurant is the downstairs dining room at the C&O Restaurant on the downtown mall. The place has been around forever, and has very good upscale comfort food. Good steaks, soups, pork chops, desserts. And you can wear jeans/shorts. There are probably several other upscale-type places on the mall, but I can't make any recommendations. Places are always closing down and re-opening there, so use your best judgment. The Ivy in on Rte 250 is a very good upscale place, too, but it is dressy. Metropolitain used to be the best upscale (but not dressy) restaurant in town. Don't know if it is still around.
4)Also on the downtown mall is a very good ice cream parlor, Chaps. Very good homemade banana ice cream, excellent black raspberry ice cream, excellent malts.
5)If Revolutionary Soup on the downtown mall is still around and you're in the mood, give it a spin. Fresh ingredients prepared by good cooks who care about their work.
6)Good Nouveau Tex-Mex: Continental Divide on Main Street about 6 blocks from the Rotunda. Great Nachos with Chili. Good fish specials, quesadillas with unusual ingredient combinations, etc. The guy who owns this place also owns a nearby brew pub that has pretty good beer and less successful (at least as of a couple years ago) food. Definitely worth checking out--I think I remember the name as Water Street Brewing Co.
7)Best Barbecue in Central Virginia: The Blue Ridge pig on Rte 20 (?) in Nellysford. This is about 20 minutes outside town, but so worth it. Great pulled pork and potato salad. Not the best barbecue I've ever had, but very, very good. Plus the old stone building is loaded with rustic charm. A great place to go after hiking Humpback rock or other nearby areas.

Good place to get good pastries and ingredients for an upscale picnic: Foods of All Nations, Ivy Road. An independent "gourmet" grocery store that churns out good fruit tarts, croissants, ganache brownies and strawberry cream tortes.
The Downtown Mall is the "don't miss" place in Charlottesville as far as eating, drinking and merriment are concerned. If you're there on a Friday evening, it will be crazy, as the town sponsors a "Fridays after 5" festival in the summer featuring local music, a lot of drinking, and total mayhem. A little like Milwaukee's summerfest, but on a much smaller scale. Just as energetic, though. The mall also has a few fun bars with outdoor seating.