South VA - Blacksburg is a quaint town, with plenty of restaurants and shops. Radford is pretty dead but the area is gorgeous. I've had a great time (even during the holiday time) in dowtown Roanoke. Roanoke has a great market area: old buildings, many cafes/restaurants, arts and crafts. I think you might be able to find pavillions / clubs for shows (check pollstar). Drive up the mountain and look over the city...Many lakes and parks down there for fishing camping, biking, hiking. (Claytor Lake, Jefferson National Forest, and an 8 mi RT hike to waterfalls in B'bg...Smith Mountain Lake - where Dirty Dancing was filmed.)
Also, Morrissette Winery is down there...and a few others I believe, if you wanted to tour.
3-5 hours
Someone mentioned the Northern Neck, I've been there - very relaxing. (Not many places to eat though.) There are a few farms to buy or pick fruit and vegetables - delicious. 2-3 hours
I also have been to Rocky Gap Resort in Cumberland, MD. It's on a golf course, lake and trail property and the rates are reasonable. 2-3 hours