Bourbon Trail Adventures: The First Time We Tasted Pappy Van Winkle!

Round three of our bourbon trail adventures! Highlights: touring the Independent Stave Company, exploring Lexington, and finding Pappy!

On our third visit to Kentucky, we hit the ground running! After meeting up again in Nashville, we drove straight to Lebanon, KY. We took a break from touring distilleries and decided to learn more about the black-charred bourbon barrels!

Postcard: Independent Stave Company’s Kentucky Cooperage

The Independent Stave Company is the largest barrel production plant in the world! We kept hearing it mentioned on various distillery tours and decided to check out their Kentucky Cooperage. To this day, this is one of the BEST tours we have experienced! We watched as the barrel staves were assembled, charred, and then held together with a few finishing touches.

Currently, white oak has been the traditionally sourced wood but that could be changing as white oak forests are considered endangered. Several distilleries such as Makers Mark, Old Forester, and Buffalo Trace are doing their best to help with forest sustainability. However, this was an aspect of bourbon making that I had not considered-the impact on white oak forests. Most of the white oak comes from Ohio but those forests are not faring well. Will they use a different oak in the future? How can we mitigate this sustainability crisis? Something to think about…

After, leaving the cooperage we stopped at Limestone Branch Distillery. (My spouse was finally able to join in on this trip, so we picked up an extra bourbon passport and got stamping!)

Limestone Branch Distillery: Producer of Yellowstone Select

The main focus of this short trip was to visit the Kentucky Cooperage and to see the Four Roses Distillery–one of my dad’s favorite bourbons. So, we continued to Lexington, KY where we stayed a couple of nights at a cute Airbnb. We were quite impressed with the cool vibe of Lexington, a small college town with a lot of charm.

Day two:

Dad made everyone breakfast and then we were off for a tour of the Four Roses Distillery in Lawrenceburg, KY. The Four Roses Distillery was ornate and designed with Spanish Mission-style architecture, which seemed a little out of place in Kentucky…but it was a beautiful facility, and we really enjoyed the tour. The guided tasting room experience was probably my favorite so far. The knowledgeable tour guide combined with the quality flavors of Four Roses…definitely a great tour! I really enjoyed the Four Roses Small Batch!

Entrance to Four Roses Distillery
Four Roses Distillery: The fermentation room, a batch of sour mash
Four Roses Distillery did a great job of explaining their mashbill recipes.

We were a little less than 30 minutes away from Buffalo Trace, so we decided to visit there again since it IS our favorite distillery! And I wanted my spouse to see what the big deal was all about!

We did a tour, tasting, had lunch on site, and toured the outdoor garden area. It really is a beautiful place, even if you don’t drink bourbon! (See previous posts for photos).

After walking around the gardens and being onsite at the facility where the Sazerac Company produces its infamous Pappy Van Winkle…we realized this was our third visit to bourbon country and we still had no idea what Pappy Van Winkle even tasted like….

We had tried in the past to find reasonably priced shots of Pappy but each time we found a place they were sold out.

We decided to try again and found a place that was advertising 1/4th of a shot for a reasonable price. We called ahead just to make sure they actually had some in stock.

Amsden Bourbon Bar: The front entrance.

We walked into the Amsden Bourbon Bar in Versailles, Ky. It was a small, studio sized bar with only a handful of tables. We sat down at the bar and discovered they had multiple selections of Pappy Van Winkle. We started to calculate how much it would cost for all three of us to try all of the available selections at 1/4th a shot. We figured this was probably our best chance considering the price and the availability. So, we went for it!

We tried the Pappy 10-year, Pappy 20-year, and Pappy 23-year!

That Pappy Moment! Our first taste of the famous bourbon!

The moment we had been waiting for had finally arrived.

We raised the first glass and cheered together! Then, like they teach on all of the bourbon tours, we raised it to our nostrils and began to smell… hmmm…yep, it smelled like bourbon.

Then, our first taste. (It was the Pappy 10-year).

I tore off a piece of paper nearby and wrote little notes for memory’s sake.


Pappy 10-year: Four Roses Small Batch? Depth. (Maybe because we visited Four Roses earlier in the day …but this sip sure reminded me of the Four Roses Small Batch as far as flavor, texture, and taste).

Pappy 20-year: Hints of caramel, smooth on the palate, long smooth finish. Reminds me of the taste of 1792 (bourbon).

Pappy 23-year: Hints of caramel, has a kick, spice, pepper?


Given its reputation and price, I thought Pappy might offer a taste sensation unlike any I had experienced before. Yet, all I found myself doing was comparing it to other bourbons I enjoy, such as 1792, Four Roses, Larceny, Elijah Craig, Penelope, and so on. I’m certainly pleased that we had the opportunity to sample the famed Pappy Van Winkle. At the end of the day, I learned Pappy is just another bourbon, distinguished only by its reputation and price point, not necessarily because of taste.

And ultimately, our search for Pappy is one of those memories that will stay with me forever.

Thank you, Amsden Bourbon Bar, for making our Kentucky Bourbon Trail dream come true!

Notes about Pappy.

We later had dinner at OBC Kitchen in Lexington, KY. We tried the baked pimento cheese and bacon dip–amazing! Returned to the Airbnb where we played dominoes and reminisced about our successful day!

Day three:

On our way out of town we stopped at the Lexington Brewing & Distilling Company (formerly known as Town Branch Distillery). They have a nice location right in the heart of downtown Lexington. They are known for their single malt whiskey.

Whiskey Flight at Lexington Brewing and Distilling Co.

Of course, if you have been following our journey, a bourbon trail adventure is not complete without a cave tour at Mammoth Cave National Park! This time we tried the Frozen Niagara Tour! (Reservations strongly encouraged).

Entrance to Mammoth Cave
Frozen Niagara Tour
A Common Cave Cricket (Hadenoecus subterraneus) at Mammoth Cave

Year 4, Round 3 of our Bourbon Trail Adventures took place in April of 2022. The memories will last forever. I love you, Dad! I love you, Val!

Stay tuned for part 5…

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