The Italian Touch has the best steak & cheese in the Valley. Cork Street Tavern is nice. The museum of the Shenandoah Valley is worth the time.
If you have time for a hike drive 20 minutes east on Rt. 7 past Berryville, cross the Shenandoah and go to the top of the mountain. At Route 601 hang a right and check out Bears Den about a mile in on the right, awesome views. When you are done keep driving south on 601 and drive by Mount Weather. Put your feet in the Shenandoah on the way back, and drink a sweet tea. Welcome to the Valley, I hope you enjoy yourself. If you do decide to check out the Mountain, go to the horse shoe restaurant on the other side of 7 on 601; don't be put off by the exterior, it is a fun place. Tell the owner Jim Wink that Bud sent you.
BTW if you are free one evening, I'd gladly buy you a beer (I'm in Berryville).