It's at the far end of the Charlottesville Downtown Mall (the place where he filmed the "Parkay" video). I currently live in Charlottesville, so I periodically head over there if I'm at the mall, and there usually are a few hundred chairs set up with a few tables, but no people hanging around unless there's actually a show going on (either the free Fridays after Five local acts or the big-name acts that sometimes come and play). I've been to only one Fridays after Five event, and it wasn't that crowded, people just kind of came and went since you didn't need a ticket or anything. I'd say there were maybe a few hundred people there, and people sometimes spill out into the far end of the mall or the side street. I'm sure that the big-name acts (that require paid tickets) attract bigger crowds. Also, the chalkboard that Chris used to draw Sonichu stuff on (and the Tomgirl symbol) is pretty close to the concert area.
Chris did visit Monticello in his "hiking" video, and I'm guessing that he has walked the UVA grounds because he mentioned it in the Ivy video (and he's also been to Alderman library at UVA). Don't know about the other stuff though.
