The two Jefferson’s Journey barrels headed down the Ohio River in June of 2016. | Courtesy of Jefferson’s Bourbon

There are several theories as to how bourbon first got its name and came to be, but the one told the most in Kentucky derives from the simple act — which wasn’t so simple back then — of shipping a whiskey distillate or moonshine down to New Orleans in an oak barrel that had been charred to cover up the remnants of whatever it held before (like fish, grains, fermented fruits and vegetables, etc.).

They’d throw the barrels onto a riverboat, and down the Ohio and Mississippi they’d go.

By the time they arrived in New Orleans, months later, the clear liquor had turned amber due to the barrel’s char. People were so enamored with the brown spirit that they requested either the “stuff from Bourbon County” (which Kentucky was a part of back then) or the “stuff they got on Bourbon Street” — historians aren’t sure of the exact reference.

Bourbon’s maiden voyage | Courtesy of Jefferson’s Bourbon

Bourbon also would be shipped down the Mississippi, out into the Gulf, around Florida and up the East Coast to New York City — and you can imagine the color of the liquid after a journey like that.

Trey Zoeller, chief executive of Jefferson’s Bourbon, always has been curious about that initial bourbon voyage over 150 years ago, so he decided to recreate the experience with two barrels full of the first distillate made at Crestwood’s Kentucky Artisan Distillery, home to Jefferson’s and a few others.

And this isn’t the first time Zoeller has tinkered with the barrel-aging process. You may recall Jefferson’s Ocean, which comes from barrels he puts on a buddy’s research ship that sails around the world. Innovation is the name of the game at Jefferson’s.

But let’s get back to Jefferson’s Journey.

The distillate was created in January of 2016, and Zoeller filled four barrels. Two were going on the trip, and two were staying home in a Kentucky rick house, as god intended.

His hypothesis, he explained at a private tasting on Thursday, was that the river, delta and ocean would impart their climate and motion into the flavor of the bourbon. It would be vastly different from the bourbon that was resting in Kentucky, even though both would be exactly the same age.

Also, Zoeller said, he wanted to pay homage “to the process that put Kentucky on the forefront of the bourbon market.”

Trey Zoeller on the trip | Courtesy of Jefferson’s Bourbon

Zoeller’s destination was New York City by way of New Orleans, Key West and the Atlantic, and the boat took off from Louisville in June 2016. The crew and the bourbon made many pit stops along the way and encountered several bad storms and even hurricanes.

At one point, the weather had gotten so brutal, the wood on the barrel heads started to buckle and the barrels themselves started showing signs of extreme wear and tear (see below).

So what did they do? Shipped two new barrels down to Florida by way of FedEx.

Zoeller himself had to siphon out the angry bourbon from the old barrel to the new, and he said it was then he knew the juice was becoming a much different product than its siblings sleeping in Kentucky.

After several months, Zoeller, his crew and the two barrels finally made it to Brooklyn, where they toasted the voyage and prepared to head back home to further analyze the barrels’ sloshed contents.

Look at the color difference between the Journey (left) and Kentucky Aged (right). | Photo by Sara Havens

Thursday night during a private release party for the latest Jefferson’s Presidential Select, Zoeller and members of Jefferson’s staff poured samples of the two 18-month-old products — called Jefferson’s Journey and Jefferson’s Kentucky Aged — which we tried side by side.

Surprisingly, or maybe not, the Journey bourbon was darker, richer and much more complex than the Kentucky Aged.

We detected a slight saltiness in the Journey, perhaps from being exposed to the ocean air, but also a rich, buttery, caramel goodness that usually only comes after a bourbon has mingled with a barrel at least five or six years.

It was an incredible experience to both see and taste the bourbons side by side, and perhaps Zoeller’s expensive little experiment (it’s not cheap to ship bourbon barrels via FedEx, he said, and they also lost a boat along the way to storm damage) proves that quality bourbon doesn’t have to be old to be good — it just has to be thrown into a hurricane or two.

Both bourbons have been bottled in 200ml bottles at 92 proof, but because there’s so little of it — just two barrels of each — Zoeller says most of it will probably be auctioned off for charitable causes, although some may make its way to store and bar shelves soon.

Jefferson’s Presidential Select is out now. | Photo by Sara Havens

In other Jefferson’s news, this year’s Presidential Select is a 16-year-old sourced bourbon that was aged in both new and old barrels. The limited-edition bourbon was fully aged 11 years in Kentucky and then put into fresh barrels for an additional five years.

We tasted this as well, and the double-cask process highlighted orange spice, molasses and tobacco notes in the bourbon, and even finished with a savory taste of crème brûlée. At 94 proof, it was smooth and sweet for a high-rye recipe.

Jefferson’s Presidential Select was introduced Thursday, Nov. 2, and retails for $199. Only 10,000 bottles are available worldwide.

Here’s a look at our tasting experience Thursday night at the Kentucky Artisan Distillery in Crestwood:

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Sara Havens
Sara Havens is the Culture Editor at Insider Louisville, known around town as the Bar Belle (barbelleblog.com). She's a former editor of LEO Weekly and has written for Playboy and The Alcohol Professor. Havens is the author of two books: "The Bar Belle" and "The Bar Belle Vol. 2."