We just decided to take a weekend in the area. My wife found out about a dinner theater event that was taking place at Buffalo Trace. It included a tour beforehand, bourbon cocktail, the play, and a three course dinner with some bourbons for $60 all-in. Good value and a fun time. We didn't keep a passport and get it stamped. However, we also fit in visits at Four Roses, Wild Turkey, Maker's and the Evan Williams Experience in downtown Louisville. At the latter, the "speakeasy tasting" was fun. Like you mentioned, I also ordered pours on my own at a couple of local bars that had nice selections. The Pappy was available at a nice restaurant called Bourbon's Bistro in Louisville.
Side note - just about everyone we came across in the area was extremely polite, friendly and fun. We had a very enjoyable weekend all around. Louisville Slugger factory tour was cool. I would definitely visit the area again without hesitation. It is an easy six hour drive from where we live.