Cigars on the Bourbon Trail

Article by Chuck Holland

It was planned as a simple road trip. Nothing more than an excursion to the heart of bourbon country in central Kentucky with several longtime herfing buddies from my two favorite cigar stores in Montgomery, Alabama. We wanted to learn how our favorite libation is created and we were excited to taste new, unfamiliar bourbons.

From the very first moments on the Kentucky Bourbon Trail, our journey of discovery and education was marvelous. We visited distilleries large and small, famous and unknown—each with its unique methods of creating bourbon. And we sampled a large, diverse, and delicious variety of bourbons.

That the outing was a huge success was not a surprise. We all expected to have fun—after all, it’s difficult to have a bad experience when good friends are gathered on a vacation whose single purpose is discovering bourbon. What was not expected, however, was how the trip served to remind us of the reasons why we enjoy and embrace the cigar lifestyle.

The very first day, during a tour of the Willet distillery, we learned that the master distiller was a cigar aficionado. We soon discovered that our experience at Willet was not unique. As we visited other distilleries we met many folks in the bourbon business that enjoy a good cigar. Most professed that their favorite smoking experiences include tumblers of the bourbons they create. With a love of cigars and bourbon in common, it was easy to strike up conversations and make new friends. Those spur-of-the-moment friendships frequently led to fascinating discussions about our favorite cigar-and-bourbon pairings led to several extended, behind-the-scenes tours.

We weren’t surprised by the cigar-and-bourbon business connection. These men and women have dedicated their lives to creating a whiskey that enhances life’s pleasures. Cigars and the cigar lifestyle are a natural fit in that approach to work and life.

We had a similar experience at a local restaurant that had been recommended numerous times during our distillery visits. Our first clue that we were in for a memorable evening came when the Harrison-Smith House told us they were full at 7:00 p.m., but they could fit us in at a later seating. We agreed. Later, while getting settled around our table, the maître d’ asked what had brought our group together. When he learned that cigars were the common denominator, he returned with the restaurant owner who introduced himself as a cigar aficionado. Soon the chef, also a cigar smoker, joined us. We spent the next hours enjoying several courses of delicious food washed down with hard-to-find bourbons from their extensive collection, while carrying on a running conversation with the owner and his chef. It wasn’t exactly a herf because nobody was smoking a cigar, but cigars were the center of discussion as we collectively investigated pairing our favorite smokes with main courses, desserts, and bourbons. The chef’s uniquely informed opinions and insights were appreciated. Eventually we exchanged addresses, handed out cigars, swapped recipes, sampled desserts, and savored a very rare, extremely old rye whiskey.

By the end of the once-in-a-lifetime evening, we had a new favorite restaurant and a slightly larger circle of wonderful smoking buddies. And it all happened because of cigars and the lifestyle they create.

Four days and many bourbon tastings later, we said goodbye to the Bourbon Trail and headed home. We all agreed the trip was an enormous success made even better by our cigars. Those cigars enriched our experiences and helped us make new friends all along the trail.

Our trip reinforced a mutually held opinion that folks who embrace the cigar lifestyle are a friendly, fun loving, outgoing bunch. No matter where they are found or what walk of life they come from, cigar smokers are bound together by comradery, fellowship, and a common interest in great taste. Those characteristics seem especially evident in bourbon country.

Our trip reinforced a mutually held opinion that folks who embrace the cigar lifestyle are a friendly, fun loving, outgoing bunch.

Michael Eman
Official Contributor
Kevin Gibson is a free-lance writer who writes for numerous publications, including Bourbon+ magazine, Thrillist, and Alcohol Professor.