OK, here are the GPX files...
So the first 150 miles (Dubois to Ohio) aren't all that. I tried to string together meandering rural highways to stay off big roads and avoid cities. But it is what it is. Feel free to consider other options to get to the north end of 164 (Lisbon or Salineville a bit south).
Then you get to the good stuff in Ohio: 164, 556, 536, 255, and 26 are the highlights. There are lots more roads in the area just as good (260, 565, 9, 147, 145, 513) but you only get one day. Your day in Ohio ends in Marietta at the Microtel (site of previous ESTx gatherings).
You hop right across the river on Day 2 into WV. 31 is pretty good, a bit of 50 east to make time, then the awesome WV16 south to I-79. Short bit of slab to Flatwoods. WV 15 over to 219. Here you can either go north on 219 and pick up 250 south or go south on 219 and take 66/28 past Cass railroad and the Greenback radio telescope to get to 250. The second option is twistier, but 66 can be dirty in spots. 250 east is excellent past Monterey and McDowell, thru Headwaters and over the last pass at the Conderate Breastworks. Continue past the overlook down the mountain until the twisties run out, then turn around (short stub). Cut north on 615 (Cowpasture Rd) road to Sugar Grove, then up CR-21 to Brandywine. A not to be missed bit of WV33 follows over the border into VA, then turn around and hit it again heading west past Brandywine and Franklin, thru Judy Gap, past Seneca Rocks and on to Petersburg. I'm sure there are a few lodging options in Petersburg but it's not a big town.
The last day heads north up the awesome Mt Storm section of 42 (Might want to repeat it), then a bit 50 over to 220 north and I-68. Your goal is Scenic 40 (aka 144) then up through southcentral PA on 26 and West Mattie Rd to the Breezewood area. 915 north to Raystown lake area. Now you're more on your own to figure out the best way home. There are big roads to make time. Rural highways for more fun. I'm sure you know your way around there.