Frankfort is 45 minutes to an hour from Winchester depending on traffic in Lexington. Several nice restaurants in and around Frankfort. We like Goodwood and Bourbon On Main in Frankfort. Call first as they may be closed due to the flooding a few weeks ago.
If you like bourbon, there are three close distilleries; Buffalo Trace, Woodford Reserve and Castle and Key. Probably no availability on tours this close but you may be able to get some tastings. If you go to Woodford or Castle & Key, The Stave Restaurant is a good lunch spot. Reservations recommended and dark on Mondays and Tuesday.
Good luck and have a good trip.
Tony