10 to 20 years ago, Kremers was a very good shop. Tons of cigars and a very healthy selection of pipe tobacco. I remember browsing through the pipe tobacco finding a lot of tins shoved to the back that were already 2 to 5 years old. I used to stop there from time to time as it was just a couple of blocks off of I65. I seem to recall there used to be a decent shop, I think it was in or near a mall, out East of downtown Louisville but before you get to the Blue Grass Industrial Park exit. It was North of 64 a few blocks. I seem to remember Oxmoor as well, nice friendly shop but not such a great selection.
I think your Son should be able to find several suitable choices where he can hang out and smoke a cigar or pipe while he is in Louisville. And depending on where he's at, other than rush hour, driving over to Clarksville or Jeffersonville isn't that big of a deal.