Just recently I was named the first “Master of the Urban Bourbon Trail” by Louisville Convention and Visitors Bureau at an event at 8 Up, the newest member of the UBT. I was awarded this title because I had been to every member of the trail and had a copy of my book Kentucky Bourbon Whiskey: An American Heritage stamped with their passport stamp. It took me about two years as I did not make special trips out just to get the stamps. That same night my girlfriend Rosemary Miller decided to start her own stamp collection in a copy of my book and to complete it by the end of September, Bourbon Heritage Month. In doing this we had several Bourbon date nights that involved more than one stop on the trail.


It started on that night, August 30, 2016. After getting the stamp at 8 Up we went to dinner at the Seelbach and then to Bourbon Raw, Sway and Marketplace for drinks and book stamps. Rosemary decided she would get a Manhattan at every stop. I decided to get the signature Bourbon Cocktail at each stop. This led to many interesting cocktails and I may have to blog about that aspect of the trail later. We stayed at the Hilton Garden Inn that night so we were drinking responsibly and not driving.

The next dozen or so stamps were done either as separate nights or maybe two or three in a day that included a lunch stop followed by a dinner stop. We had several favorite places such as Bourbons Bistro and Volaré, which are across the street from each other but are frequent stops for us even when not on the quest. The patio at bourbons Bistro is a favorite place for me to enjoy a Bourbon and my pipe and Volaré has great food and Rosemary loves their barrel aged Manhattan.

The next big date night was a double date with Maggie and her husband Jordan, who made an excellent designated driver. We did four stops in the same block at Main Street and 2nd street. We started at O’Sheas and had dinner, then to Doc Crow’s next door, around the corner to the Side Bar and finished at the Troll Pub. We were not impressed with most of these places and Doc Crow’s stood out as the highlight of the evening. The signature cocktail is one the best on the trail and the wait staff was very attentive even though it was a busy Saturday evening with a U of L football game at Marshall bringing out the crowds to watch the game with friends. This friendly attitude really made the place an enjoyable visit.

As the month drew to an end we did a couple of special trips to get stamps. Rosemary’s favorite was out to Buck’s in Old Louisville. It was a trip for a drink and the stamp after having been to dinner. It was eight  o’clock on a Monday evening and the place was not busy with only a few other people in the place. The waiter actually did bartender duty as the regular person had left for the evening. Even so he made Rosemary an excellent Manhattan and an enjoyable signature cocktail. Rick Bartlett was playing the piano and singing some classic songs at the bar. It really did make for a magical experience.

The final big push was made as the month drew to a close. Rosemary decided we would get seven of the last eight stops in one evening. We got a room at the Galt House and then hit the streets. The first stop was Proof at 21c for cocktails and an order of fries as an appetizer. Rosemary had a Pikesville rye Manhattan that was excellent. The next stop was at The Bristol Downtown where the bartender did an excellent job on making the cocktails making sure Rosemary’s Manhattan was made the way she liked it with plenty of cherries. We also had an order of their green chili wontons to keep us fortified for the night. Next stop, Vincenzo’s for some more great cocktails followed by cocktails and a small complimentary appetizer tray. Next in order was to get some food as well as cocktails at Blu at the Marriott Downtown. Gnocchi for me and a pizza for Rosemary. After dinner the next stop was Bistro 301 where we had cocktails at a sidewalk table while I enjoyed my pipe. Next was Down One Bourbon Bar and a final stop at Jockey Silks in the Galt House. It was a great time but we both admit that it should have been broken down into two evenings to make each stop more enjoyable. All of these stops had their own separate personalities and charms and deserved more than the half an hour to 45 minutes we gave them that night.

Rosemary made lunch at Lilly’s her final stop on the Urban Bourbon trail on Friday September 30. She is friends with the owner, Kathy Cary who besides being a talented chef, a pioneer in farm to table food and a very nice person, is also a member of the Thompson family who used to own Glenmore Distilleries before it was sold to united Distillers in 1992. We had an excellent soup and sandwich lunch with Rosemary stating the Manhattan was one of the best on the trail and the signature cocktail was also one of the best on the trail. She had completed the trail in one month.

Bourbon date nights while on this quest were a lot of fun and often very romantic. I am not sure that doing seven stops in one night is a good thing to do unless you make some of the drinks coffee. Even better take it one step at a time and enjoy the romance and ambiance at some of these places such as Buck’s, Varanese, Volaré or Bourbons Bistro. A bourbon themed date night can be fun and romantic. Enjoy!


Photos Courtesy of Maggie Kimberl