In Winchester, try Vivian’s Country Cooking, if it’s still open. Cafe Sofia serves Bulgarian food, which is probably the last thing you’d expect to find in this part of the country.
Just south of Winchester on Rt. 11, the Wayside Inn in Middletown serves a great country ham and can be a bit of a splurge but is definitely worth it. Over in Front Royal, the Royal Dairy has been going strong since the 40s.