Southern Pa-Greenville, NC-everything in between

The week of August 10th I will be heading down to Greenville, NC from WNY and will be taking back roads.  I am looking for suggestions near or on our route.  I like anything small town, old/historical, cheap, regional, indoor/outdoor seating... you know, typical road food stuff. 

I will be on Route 522 crossing into Maryland and through West Virginia and Virginia.  Any suggestions for places on this route?  Hancock, MD and Berkeley Springs, WV along with Winchester and Front Royal are a few towns I wrote down that we will pass through if this helps you know where we will be. 

In Virginia we will also be going from 522 to Route 360, 460 to 46. 

46 will take us into North Carolina and through towns like Roanoke Rapids and Garysburg. 

Any must stop eats or must sees that are not food related?

Thank you everyone!

A great old “Meat & 2” in Hancock, MD, is Weaver’s Restaurant and Bakery.  Great food and atmosphere – everything from sandwiches to soups and salad to full meals.  And their baked goods are just as good.  Get several dozen raisin cookies to go.  Also in Hancock is Hepburn’s Orchard & bakery – delicious pies and lots of jellies/preserves etc.  Both highly recommended.
http://www.weaversrestaurant.com/
http://www.hepburns.com/

Thanks for the suggestions.  I will definitely keep it in mind, especially since there are baked goods involved! 

I have also found the Frost Cafe in Culpeper, VA.  Anyone ever eat here?  The photos make me want to stop.
http://www.choppedonion.com/id77.html

Also, what is a wing ding?