Kentucky Bourbon Trail: Location 2 - Louisville

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.

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.

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!

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!

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.

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!

Kentucky Bourbon Trail: Location 1 - In and Around Bardstown

I suspect everyone close to me was getting tired of hearing it: I am going on the Kentucky Bourbon Trail! Well, I am back from Kentucky! Having concluded two stays, one in Bardstown and the other in Louisville, I feel like I had a very satisfying and balanced trip. This cigar blog will look at my bourbon tasting and cigar smoking in two parts, based on two locations: Bardstown and its "outer bourbon region," and Louisville. 

Milwaukee Departure, Maker's Mark, and Bardstown:

I left Sunday morning by about 6:45 am and cruised through Wisconsin, Illinois, and Indiana without incident. I snacked in the car and stopped twice to use the rest room and get gas. The plan was to drive directly to a tour at the Maker's Mark Distillery, and then after that to check into my hotel in Bardstown. On the way to Maker's, I drove through Bardstown and proceeded about thirty minutes south/southeast of Bardstown, in the vicinity of Laretto, Kentucky. The Maker's Mark Distillery was literally in the middle of nowhere, only accessible via narrow and winding roads without shoulders. These roads would pass for bicycle paths in the Milwaukee area, but they had posted speed limits from 35 to 55 mph. I was not used to driving like that. When I got to the distillery, I was still surprised how small it was, despite the fact that my mind should have been primed by the remote area.

The tour was interesting. Much of the work was still done by hand, from dipping the trademark red wax seals to handcranking the printing press for making the labels. The tasting at the end was very good, as I sampled four types of whiskey, and finally purchased two bottles. I will say more about all the whiskey I bought on this trip in later posts: I was surrounded by so much bourbon, so if I was gonna get the chance to smoke a stick in Kentucky, I was gonna pair it with other bourbons that I could find there. I will pair the whiskey I bought with cigars back home and share out later.

Maker's Mark Distillery

After Maker's Mark, I returned to Bardstown and checked into the Talbott Inn and Gift Shop. This hotel got its start as an inn in 1779 and has a restaurant, tavern, and gift shop attached to it. Sunday is a quiet place for Bardstown as most businesses, including all the other restaurants, were closed. Talbott's restaurant was the only one open, so naturally it was packed with tourists and locals alike. I waited patiently and ate a Kentucky combination plate: three sliders - one was fried green tomato, another pulled pork, and the third was ham and swiss cheese. Very tasty.

 Otherwise, there was only one liquor store in town that sold good cigars, and it was also closed on Sundays; so I prevailed upon a cigar I brought from home, a My Father Flora de las Antillas Toro. I snuck outside a side door facing the eastern sky and a waxing moon. I had already had plenty of bourbon at Maker's Mark so I just sipped on water as I enjoyed the mild, creamy flavor of this My Father. The Talbott is on a main street in Bardstown, and this eastern side door opened up around the corner at the beginning of a residential area. I don't like to be that annoying cigar smoker who disturbs people who prefer a smoke-free space, but the door was far enough away from the neighborhood homes, and there was no traffic in and out of this side door.

Enjoying a My Father outside the Talbott Inn, Bardstown, KY

Then I thought I was busted! An older couple rounded the corner, and the woman said to me, loudly, "That's you!" Her neck craned and nose sniffed the air.

I sprung up from the stoop to move away, waving away my cigar smoke. "I am so sorry," I said.

"No, no," she said. "If it is pipe or cigar smoke, I love it."

"That's a My Father," said the husband. "Did you get that in town, here?"

"No," I said with a sigh of relief. "I brought it from home."

They were from Delaware, and after brief small talk about the closed liquor store, both he and I expressed the intent to check out the store's humidor before leaving town. They excused themselves, and then I finished the My Father and turned in for the first night.

Woodford, Louisville, and back to Bardstown

On  Monday, Day 2, I awoke bright and early. I exercised and ate breakfast at the inn. Then I drove an hour west-northwest to Versailles, Kentucky. The roads were narrow with high speed limits, but the Woodford Reserve Distillery was located in the middle of Kentucky ranch country. The roads were only a little bit wider than the ones leading to Maker's Mark. The scenery was filled with lush pastures populated by beautiful horses that were grazing, walking and trotting.

Although Woodford Reserve was founded in the 1990s, the distillery is on a site that had been in the distilling business since the early 1800s. Many of the facilities are new, but some of the old buildings from the 1800s were still in use. Therefore, the site was very beautiful and historically rustic. The operation here was again smaller than I expected. (By contrast, Jim Beam, which I did not tour, but drove by, looked like a small city). The Woodford tasting was also delicious at the end, and I bought one bottle. Again I will write more about these purchases in later posts! 

A Cohiba Weller with Elkwood Reserve Bourbon; Volstead Lounge in Bardstown

Later on Day 2, I went to Louisville for a while, ate a late lunch, found a cigar bar, and toured another distillery, but those will be featured in the next post about Louisville. Later when I finished in Louisville on Day 2, I returned to the Talbott Inn in Bardstown. I took a break and then walked over to the liquor store which had an impressive humidor. I bought a Cohiba Weller, a little pricier, but I was in bourbon country, and this cigar's tobacco was aged in bourbon barrels. Then I went to the Volstead Bourbon Lounge, a tavern with an intentionally cramped and covert feel, like a speakeasy. They also had seats outside on their storefront, so I ordered a Bluegrass Elkwood Eleven Year Reserve to pair with my Cohiba. Now I know many of you are wondering if I asked the bartender if they had Weller Bourbon, which would have made sense. I didn't! When my eyes caught that Elkwood 11, I jumped at it!

I sat out front, and lit up the cigar. It's initial lighting bite was spicy; I could definitely taste the hint of spice and liquor on it from the bourbon barrel aging process. And then when paired with the Elkwood, it gave me fine buzz that carried me from the Kentucky twilight, through dusk, and well into the dark night. It is a robusto size, if I remember right, and it smoked for a good 80-90 minutes. I walked back to my hotel and ate some sandwiches I brought along from Wisconsin. It was 10pm by this time and all the dining in Bardstown was already closed. 

Cohiba Weller - hints of bourbon and spice.

That was my trip to Kentucky, summarized for the Bardstown region. Coming soon - the Louisville experience!