Matthew Landan and his ultimate Pappy experience | Photo by Sara Havens

From the high rollers to the penny pinchers flocking to Louisville this week for the Kentucky Derby, chances are they know at least two things about bourbon: 1) Kentucky is where most of it is made, and 2) Pappy.

Haymarket Whiskey Bar owner Matthew Landan is hoping to catch the eye of some of these thirsty high-rollers with his ultimate Pappy experience. For $5,000, a group of up to four people can enjoy an ounce pour of each of the six Van Winkle bourbons, plus a pour of the super rare Old Rip Van Winkle 25-year-old bourbon that was released this month — but more on that in a bit.

All this could be yours $25,000. | Photo by Sara Havens

The package — which is supposed to be experienced at the NuLu dive — also includes one bottle of the rare Bourbon County Brand Stout, a four-pack of beer of their choice, a round of cigars, T-shirts, an Uber ride home and four bottles of Buffalo Trace products (Eagle Rare, Blanton’s, E.H. Taylor Small Batch and Sazerac Rye) meant to be taken home.

“And we’re throwing in unlimited pinball play, too, for the authentic Haymarket experience,” Landan enthusiastically adds.

There are only three of these Pappy escapades available, and it’s first-come, first-served, says Landan. And say someone wanted to buy the whole kit and caboodle — purchase all the bottles Landan has set aside for this event? That price tag will only set you back $25,000.

The extremely rare Old Rip Van Winkle 25 | Photo by Sara Havens

And now, back to what inspired this madness. Haymarket was one of a few bars locally to receive the Old Rip Van Winkle 25, which Landan calls “The mother of all bourbon.”

Only 710 bottles were produced, and if you’re lucky enough to get your hands on one, they’re selling on the black market for upwards of $10,000.

Landan knows of a bar in Atlanta that is selling 1-ounce pours for $1,200. The oldest of the Van Winkle offerings, the bourbon comes in a fancy case and crystal decanter.

The other six brands of Pappy the lucky few will get to taste include: Old Rip Van Winkle 10 Year, Van Winkle Special Reserve 12 Year, Van Winkle Family Reserve Rye 13 Year, Pappy Van Winkle’s Family Reserve 15 Year, Pappy Van Winkle’s Family Reserve 20 Year, and Pappy Van Winkle’s Family Reserve 23 Year.

(For an in-depth read about the difference between Pappy and the Old Rip Van Winkle brands, check out Louisville bourbon historian Michael Veach’s blog post on the topic.)

If you’re interested in the ultimate Pappy experience and have the cash to burn, contact Landan at [email protected] And if you need an extra member of your party, please keep us in mind.

Haymarket is located at 331 E. Market St.

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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."