Paying Bourbon Forward: The Stranger, Mom and the Wilderness Trail Story

By Kevin Gibson

A few weeks back, I shared a new bourbon with a friend. His bourbon journey is still getting out of the gate, but mine is into probably the second furlong and I wanted to give his a boost.

What I wasn’t expecting was a story that would unfold afterward and, in an unexpected way, come full circle, in a profoundly personal and emotional way.

That bourbon we shared was Wilderness Trail Single Barrel, which for my palate is basically just 750ml of bottled-in-bond magic presented in a square glass vessel. My friend, Butch, tried it and liked it so much – this is a guy whose relationship with whiskey generally meant pounding it in college – that he asked for a second pour. Which meant I’d done my job. I ended up later buying a bottle for him and his wife (a bourbon lover) as a gift.

Well, as it happens, I work part-time in a bourbon shop in Louisville, Ky. (by the way, the next time you’re in town, you definitely want to check out Taste Fine Wines & Bourbons), so I get to try a lot of whiskeys; that’s how I found this particular Wilderness Trail. So when a batch of Lion’s Share bottles landed in the shop, I was naturally intrigued. The Family Reserve version of the single barrel presented itself with an age statement of four years, four months, bottled at 111 proof. Only 241 bottles went to market. Six landed at Taste.

As this was not a bottle the shop’s owners opted to open for pours (there are already more than 260 open bottles at the shop, so I get it), I had little opportunity to taste it lest I take a chance, fork out the cash and buy a bottle. The pandemic having taken a toll on my bank account, I tried to look away as bottle after bottle went out the door in the hands of others.

One Sunday afternoon about three weeks ago, I was working – not my usual shift, mind you – and a man came in from out of town looking to take some bottles home with him. I let him try a couple of bourbons unfamiliar to him, and he didn’t much care for them. Then he asked me my personal favorite, so I introduced him to my beloved Wilderness Trail single barrel. He said, “I’ll take a bottle.”

“Do you want to try it first?” I asked him.

“Nah, I trust you.”

And then he noticed the Lion’s Share bottles, of which only three remained – one small batch and two single barrels. He asked about them and I explained what they were and their relative scarcity.

“I’ve been dying to try those myself,” I remember telling him, “but since we don’t have them open, I guess it’s not going to happen.”

“I’ll take one of each,” he said.

He paid for his bottles, I began to bag them up, and he said, “Is it OK to open these here?”

I was confused, since he had told me when he walked in that he was on the road and just wanted to stop in to grab a bottle or two.

He continued, “You said you wanted to try them – let’s try them together.”

So we opened the bottles and stood there for 20 or so minutes, sipping and discussing the differences in the two, the flavors, talking about our favorite other bourbons. We agreed both were excellent, but the single barrel was the favorite of the tasting for us both. And then I bagged up the bottles and he was on his way.

To me, the experience exemplified what I’ve long learned that bourbon is about: People coming together, sharing. It was perfect example of bonding over bourbon.

Naturally, I was then even more interested in buying that last bottle. As it happened, a couple of days later, my girlfriend Cynthia needed to take her car to the mechanic. I met her there early on a mild, sunny morning and as I drove her back home, I told her the story of the guy who came in and shared his bourbon with me. She agreed it was a wonderful story.

I said, laughing, “The bad thing is, now I want that bottle more than ever.”

“Are you going to buy it?” she asked.

“Nah,” I said. “I have enough bourbon – I don’t need to spend that money right now.”

And that was it. I told the story, made the decision to be a grown-up and not spend the money. Was I still tempted? Well, of course. But when I make a decision, I don’t look back.

This is where the story gets very personal. You see, my mother died in May after a valiant three-plus-year battle against lung cancer, COPD, congestive heart failure and, finally, brain cancer. She died on Mother’s Day. It was not a good day for my family, and her memory is still very fresh in my heart as I type this.

Well, when I drove Cynthia back to the mechanic later that day to pick up her repaired car, I pulled into the lot, she got out and said, “Don’t leave. Wait for me.”

So I waited, presumably to satisfy her ADHD impulse that something might not be right and she would need a ride home. I buried my nose in my phone, reading sports news. After a couple of minutes, she walked back over to my car and got in. She had been thinking about my story all day, she told me, about the guy who shared his Wilderness Trail with me. And then she reached into her purse and pulled out her wallet. From her wallet, she presented me with some cash. Once again, I was confused.

Thank you, Mom.

“This is the money your mom gave me last Christmas,” Cynthia said. “I’ve just been sitting on it. I want you to take it and buy that bottle of bourbon for yourself. It will be like your Mom is buying you one last gift.”

And then I sat in my car and cried as she rubbed my back and cried with me. It’s a moment I won’t ever forget, an act of kindness that had come full circle from a different act of kindness by a stranger.

Needless to say, after I dropped Cynthia off, I went straight to Taste and bought that last bottle – bottle No. 15 of 241, to be exact.

I haven’t opened it yet; I’m waiting for the right moment. Christmas? My parents’ anniversary? Or just after a particularly rough day? For now, I just love having it sitting on top of my bar, because I can enjoy this memory every time I walk past. I think of the out-of-town guy (I’m embarrassed to say I’ve forgotten his name) and his generosity, Cynthia’s act of sweet thoughtfulness, and then relating the full story to my Dad and aunt over dinner, only to have them tear up as well as we sat together and remembered my departed Mom.

Cynthia’s not a bourbon drinker, so she is hesitant to try a sip of the new bottle of Wilderness Trail Family Reserve she and Mom gifted me. But I can’t wait to share it with my friend Butch, so the story can continue on.

Kevin Gibson is a Louisville, Kentucky-based author and freelance writer who writes about everything from food to beer to bourbon to the great city he calls home. In his three-plus decades as a writer, he has won numerous awards but doesn’t know where most of them are now. He is author of Louisville Beer: Derby City History on Draft, Secret Louisville and several other books. He currently lives in Louisville’s historic Clifton neighborhood with his dog, Atticus.

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4 Replies to “Paying Bourbon Forward: The Stranger, Mom and the Wilderness Trail Story”

  1. My eyes seem to be leaking for some reason. That wonderful woman Cynthia and the memory are keepers. Hold on to them.

  2. I am sorry for your loss.
    Great girlfriend , thanks for sharing your story. Enjoy the bourbon.

  3. I think your Mom is smiling. You’ll feel her nearness when you have that first sip.
    Wonderful article, as always.

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