Winchester proper is kind of a fast/chain heaven. The places that I know of are a bit southerly of Winchester on 1-81. First is the Wayside Inn on the Middletown exit along with the mucho wonderful Route 11 potato chip place, a must have for take home.
A bit on further is the Strasburg exit and the Strasburg Hotel, a grand old hotel with great prices and delicious food……love their frizzled onion rings
then just a wee bit further is Woodstock which has an old fashioned soda fountain drugstore and the Spring House Tavern. as well as Shaffer’s, a small grocery where you can get deli country ham sandwhiches and biscuitsa
All are located along Rt 11 off of 1-81
Maximum mileage is to the Spring House. which is approx 30 miles from central Winchester