As promised, this post is the "Part II," or Location 2, of my Kentucky Bourbon Trail trip, focusing on the Lousiville Experience. If you read the previous post, you are already aware that these write-ups are not in chronological order, but rather framed by location. Last time I outlined Location 1, the Bardstown Region: on Day 1, I toured Maker's Mark and enjoyed a cigar outside the Talbott Inn. Then on Day 2, I chronicled my tour of Woodford Reserve and later the Volstead Bourbon Lounge, where I paired a Cohiba Weller with Elkwood 11 Year Reserve.
This post will take us back to the middle of Day 2, with my late afternoon-early evening in Louisville. Then it will take us to Days 3 & 4 for my full adventures within, and eventual departure from, Louisville and ultimately the conclusion of my Kentucky trip.
Departure from Woodford, Daddy Crow's and Havana Jack's
The first segment of Day 2, Monday, ended in Versailles, Kentucky, when I left the Woodford Reserve Distillery and traveled west-northwest to Louisville, with my main goal being a tour at the Angel's Envy distillery in downtown. This was probably the most poorly planned part of my trip: I got to Louisville with well over two hours to kill before the Angel Envy's tour. I planned, and really enjoyed, a late lunch at Daddy Crow's Southern Smokehouse and Raw Bar, where I banished my hunger with a most delicious helping of Kentucky's comfort food - country fried pork chops! (Highly recommended!) However, there was no way lunch was gonna fill all that time. My cigar-smoking time in Louisville was not scheduled until Day 3, Tuesday (outlined below). But sometimes instilling a splash of chaos to any lesson, ritual, or dance, allows Heaven and the Universe to guide you! I walked out of Daddy Crow's, fully satiated, and headed toward Angel's Envy wondering what I was gonna do for an hour and a half. And then there it was, completely by coincidence: a cigar bar that did not come up on any of my internet searches while planning my trip: Havana Jacks.
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| Smoking a candela at Havana Jack's, Louisville, KY |
Havana Jack's Cigar Factory was located a few blocks right in between Daddy Crow's and Angel's Envy on Main Street in Louisville. It is owned by Jack, a charming young man. He sells a variety of good cigars, but specializes in blended candelas. With seed from Cuban tobacco, these cigars are a blend of tobacco grown in Kentucky descended from those seeds, and other tobaccos imported from Latin America. The candelas are harvested early, before the tobacco is ripe, which makes them green in color, and much more mild in flavor than standard cigars. (I did not know this until he educated me!). So I stayed and smoked one, along side sipping some bourbon, Monk's Road Single Barrel.
The candela was very mild and very smooth. If you are new to cigar smoking, I recommend them. If you are gonna smoke four or five sticks in one night, I recommend them. Havana Jack's in Louisville has a website if you want to check them out and order some.
As for the bourbon Jack served me, apparently this whiskey originated historically partly on purpose and partly by chance. The Dant family, who founded Monk's Road, lacked the money to make a traditional copper still in the 1830s, so they hollowed out a big log and distilled their bourbon in it. When descendants of the Dants revived the company in 2021, calling it Logstill Distillery, they no longer use log stills. However, they are built on the old Cold Spring Distillery site, which has access to spring water coming from limestone rock beneath the ground. Now, while all the distilleries I toured discussed the importance of limestone infused spring water to bourbon production, I have to assert that Monk's Road was the most "earthy" tasting bourbon I have ever sampled. And this flavor is explained, by various online sources, by the limestone. I highly recommend trying Monk's Road Single Barrel Bourbon.
Finally to Angel's Envy
After bidding Jack goodbye, I walked a few blocks into the Angel's Envy downtown distillery. Compared to Makers and Woodford, which were full-process tours, this experience at Angel's Envy was intended specifically as a "flavor tour." This session only paid superficial mind to the entire distilling process, and rather focused on the aging and flavoring of the bourbon. The tour is called, "The Art of the Single Barrel." The guide had us sample the product at various stages. We sipped the port wine used to flavor the inside of the barrels. Then we sampled the clear grain alcohol that came from the stills, and after that we sampled the unfiltered bourbon straight from a barrel. And finally, at the end, we did a standard tasting just like the other tours offered. I bought one bottle of single barrel for myself, and another for my brother-in-law. (It was his birthday while I was down in Kentucky). I will let you know how this pairs with cigars later on when I open it. At the conclusion of Angel's Envy, I traveled back to Bardstown for my final night there.
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| Ready to sample unfiltered bourbon, straight from a barrel. Angel's Envy, Louisville |
Hiking, the Bourbon Barrel Inn, and the Louisville Cigar Company
On Day 3, Tuesday, I awoke, ate breakfast, and checked out of the Talbott Inn. I spent the morning hiking 7.5 miles in the Bernheim Forest and Arboretum, a beautiful wooded area in the Clermont area of Kentucky. If you like to incorporate exercise and nature into your bourbon and cigar lifestyle, then this is a great interlude. After I finished the hike, I had some time to kill and I was very hungry so I stopped at Zaxby's Chicken in Shelbysville. I was told by a girlfriend in Wisconsin to sample it, even though it was a fast food joint, as it was a common Southern experience. It was comfort food that was tasty and filled my tummy.
After lunch I made my way north to the Bourbon Barrel Inn Bed and Breakfast in the historic neighborhood of Louisville known as "Old Millionares Row." This place was amazing! It was a beautiful renovated mansion from the Victorian Age. The owners Brian and Rich came out and greeted me at the front door and showed me around. They invited me to their cocktail hour with great bourbons, other spirits, and homemade appetizers - all on the house! After I cleaned up (I had been hiking, remember), they entertained me with great conversation in an adorable sitting room with a beautiful wood minibar. They shared two amazing Kentucky Bourbons with me - and for now, I am keeping these a surprise for my readers, should they venture to Louisville to visit these guys. You will have to trust me that their selection of spirits was impressive! Later they offered guidance and advice to help me navigate my way to the Louisville Cigar Company via the city's rideshare options. The next morning (Day 4), they made a delicious breakfast and bid me farewell as I resumed my Kentucky travels. I will visit these guys again - they know how to run a bed and breakfast! I felt like part of the family!
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| Eggs Benedict at the Bourbon Barrel Inn, Louisville |
After cocktail hour at the Bourbon Barrel Inn concluded, I traveled to the Louisville Cigar Company and Speakeasy on Baxter Avenue. This was the "main event" of my trip, if I had to pick one. The establishment was divided into three areas: 1) the humidor, where I purchased a huge LFD Double Ligero 700 Natural; 2) the speakeasy, where I ordered a double Michter's Small Batch Straight Bourbon; and 3) the cigar lounges, three of them, where I found a seat facing a big window overlooking Baxter Avenue. Here I felt like a queen. I have had LFD Double Ligeros before, and I chose one at this moment for a reason: this cigar is just about the boldest smoking experience I could possibly imagine. After sampling plenty of bourbon at the bed and breakfast already, I needed something strong to pair with the Michter's. This was the climax of my spring break, finally landing at the Louisville Cigar Company. The buzz of the bourbon(s!) and the Double Ligero hit me with an intense, yet gentle, state of contentment and well-being. The smoke carried me well over an hour until closing time, and its kick is known for putting a lot of aficionados over the edge, so to speak, with sweats or jitters. For me, this manifested as a sudden, ravenous appetite. This was all part of the plan, because a short walk away was Molly Malone's Irish Pub and Restaurant. They had late night dining, so I stepped right over and had a corned beef sandwich and chips (fries), a crazy encore to St. Patrick's Day as I now approached Easter! After my appetite was satisfied, I returned to the bed and breakfast and fell asleep with smile on my face. Check out this cigar company and Baxter Avenue!
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| The potent LFD Double Ligero 700 Natural |
Honorable Mention: Big Red Stables
On Day 4, I checked out of the Bourbon Barrel Inn after the amazing breakfast I mentioned above. Before heading home, I drove to the Harrodsburg region of Kentucky, about an hour southeast of Louisville. I wanted to go horseback riding, and although this does not pertain to bourbon or cigars in the least, I wanted to give this experience an "honorable mention." The Big Red Stables, owned by Emily and Drew, is a 110 acre ranch that offered a personal 90 minute tour of its scenic ranch on horseback. This was not a mundane trail ride, like you might get at some of the bigger, corporate stables, where the horses walk along like drones. Drew took me out and we rode throughout the ranch, across pastures, along wooded areas, and even along a creek, with water splashing like a Western movie. He was a good coach and impressed upon me the importance of always "standing in the stirrups" because the horses did not have blinders on them and were easily startled. (I believe my athletic background as a track and field athlete helped me with this too). The ride was exciting, yet serene and relaxing. I want to go back to Kentucky for the bourbon and cigars, but I will certainly ride with Drew again, too, at the Big Red Stables.
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| Riding the filly, Taylor, at Big Red Stables, Harrodsburg, KY |
Conclusion
After I dismounted and settled up with Drew (his ranch is family-owned and "cash-only" for the ride), I got in my car and I headed home! I hope you enjoyed the summaries of my wonderful experiences in Kentucky as part of my own self-planned bourbon and cigar trip. I will expand on the bottles of bourbon I purchased while on this trip in later posts. So stand by!





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