Hello, just saw this.
Lot's of good riding, but not so many great routes out of town. If things are quiet, you can head out on 20 south to 53 and ride past Monticello. Most people will then go south from there. 631 Old Lynchburg Rd is a very popular escape route. After that, I would recommend taking Old Ivy to Garth. Garth is busy until you get to Hunt Country Store (where Garth meets Free Union Rd). Ivy (250W) is actually not that bad. Another good ploy is to ride Ivy to either Old Ballard or Broomfield roads.

We have some rides on mapmyride as VACycling. One of my favourites is to take Ivy to Bloomfield to Dick Woods and then onto Batesville store via Miller School. Then take Plank, go across 29S and go home on Old Lynchburg or abbreviate it via Plank to Edge Valley to Taylors Gap to Redhill to Dudley Mountain to Old Lynchburg to home.

I would also highly recommend the ride to Afton. If the weather is good, there is an awesome ride starting from Batesville. Go south into Nelson county towards Wintergreen. Then keep going on 151 until you can take a right that will take you onto 56 and Tyro. Then go up Crabtree Falls highway and take the Parkway back to Reeds Gap. Zip up and descend Reeds back to Wintergreen and eat at Blue Ridge Pig. This is a v. hard ride though. You could start it in Wintergreen if you liked.