That's my hometown, so I've got a bit of advice.
Highway 250 West is nice. Pick up Plank Road East. It'll be on your left by a large white roadside fruit stand. You can jump off of Plank Road and take Edge Valley, which is twisty and fun, but watch out for slow moving farm equipment and North Garden Board Meetings (two cars stopped in the road next to each other while their drivers chat.)
Edge Valley will take you to 29, and you can take 29 south for a couple of miles and pick up Plank Road again.
You can also just stay on Plank Road. It also goes to 29 and continues on from there. Keep following Plank Road until it ends at 20. From there you can turn north and get back to Charlottesville, or you can go south and do some exploring.
Have fun!