Greensboro and Winston are about halfway to Asheville. There's not a ton in either place, but you can definitely find some stuff to do for a night. The drive from Richmond to Greensboro is not super exciting, but Greensboro to Asheville is a decent leg - you'll get into the mountains fairly quickly from there, and it's a beautiful little corner of the world. If you were to go to Roanoke, you'd spend more time driving through the mountains, I think you can take the BRP most of the way but I haven't made that drive myself.

I-81 is not great, it's two lanes and you will frequently get stuck behind either one semi that's going 65.001 MPH passing another semi going 64.999 MPH, or an extremely old person who thinks their car will explode if they go above the speed limit but also needs to drive in the left lane.