Schwab is the best tobacconist in town but they are located in a weird part of town.
The Lexington Cigar Store is right downtown across the street from the Public Library. One stop shopping for porno mags, sex toys and cigars...it's like heaven on earth!!!
Strauss has a shop in the Rupp Arena shopping complex. The lounge there is decent and, considering the smoking ban in Lexington, it's not a bad place to sit and have a smoke. They usually have a good selection.
I don't get to Lexington much for dining but if you are there this coming weekend then you really need to consider heading to Keeneland to take in some horse racing. If you have never been there before then the beauty of the race track, the beauty of the nearby horse farms...really, it's worth the trip. The funny thing is that Keeneland is rather on your way to some of the distilleries. Woodford Reserve, Buffalo Trace are not terribly far from there. Trust me, Keeneland is classy and with good weather you will have lots of eye candy.
I guess that if I were to offer suggestions on dining then I would suggest a few of the long established local places: Joe Bologna for pizza; Ramsey's for Kentucky cuisine; Atomic Cafe - sort of a Caribbean fusion thing...there are a few others that come to mind but I am not sure what you are looking to have.
Enjoy your trip...