I love Winchester! We eloped to Winchester.

I haven't tried most of these, since we don't get there that much, but they sound interesting enough that I'm thinking this year, for our anniversary, we may need to go back, in part to try them.
Brewbaker's Restaurant
168 North Loudoun Street
Winchester
(540) 535-0111
Piccadilly's Brew Pub & Restaurant
125 E Piccadilly Street
Winchester
(540) 535-1899
Cork Street Tavern
8 West Cork Street
Winchester
(540) 667-3777
Then, there's the usual chain restaurants too. If you have time, spend some time walking around Old Town.