Bourbon Trail of Tears


My trip to Kentucky during Derby weekend was like your typical episode of “24.” Except all out of order.

There was a constant countdown ticking away the seconds to the next distillery, the next free drink (just 2-4 oz.), the next race, the next losing bet, the ridiculously early 8 a.m. tee time scheduled on Sunday after the Derby. It might have been my wicked hangover, but you could practically hear the thunderous echo, like a hammer pounding on an anvil inside my skull. Ping! … Ping! Commercial.

There was torture … or enhanced interrogations, if you prefer.

  • Exhibit A was Buffalo Trace White Dog, which was so harsh it practically sizzled as it trickled down my esophagus. It was clear and looked as serene as Lake Placid inside a little shot glass, which should’ve been my first warning.
  • Exhibit B was the Woodford Reserve distillery, which looked less like a place you made booze and more like a bomb had exploded inside a Potterybarn. I resisted the urge to buy a tchotchke engraved with “WB,” for fear of someone calling me out as a wanna-be “white boy.”
  • Exhibit C was the Four Roses distillery, where we were subjected to a massive vat of smelly, cream-colored crap, but would eventually become beautiful bourbon (below).
four roses

Four Roses vat of stuff that smelled awful, but would taste good after a visit from the bourbon fairy.

Like a typical “24” episode, the weekend also featured a lot of screaming. I wailed about injustice a lot, especially when my picks lost 11 out of 12 races on Oaks Day, which is held the day before the Derby. Oaks draws many locals who don’t want to subject themselves to what could easily be the most densely populated infield shit-show this side of the Daytona 500.

We were in the bleachers, which provided easy access to place bets, sip beer and mint juleps, and safely watch the horseys gallop without catching an STD or getting shanked by pastel-wearing ex-cons.


Lots of big hats at Oaks Day.

Other folks in my crew screamed like schoolgirls when they saw little garden snakes in the bushes.


Bourbon is one of the few liquors I can drink neat and not cringe as it trickles into my belly. From Maker’s Mark to Four Roses, it has a certain … I can’t say sweetness, because some are definitely not sweet. Maybe tasty is a better word.

bourbon02There are a few ground rules. By federal law (as every Kentucky distillery will remind you), bourbon made for consumption in the good ol’ U.S. of A. must be:

  • Produced in the United States.
  • Made from a grain mixture that is at least 51% corn.
  • Aged in new, charred oak barrels.
  • Distilled to no more than 160 proof (or 80% alcohol by volume).
  • Entered into the barrel at no more than 125 proof (62.5% alcohol by volume).
  • Bottled at 80 proof (40% alcohol by volume) or more, like other whiskeys.

A lot of care went into establishing those standards. My drinking companions and I, however, failed to exercise much diligence or judgment at all in crafting some rules of our own for the weekend, all of which were violated at one point or another during our journey down the Bourbon Trail:

  • Bros before ‘hos (even funnier because half of the group were women).
  • Don’t let a grown man wear a lady’s hat.
  • Eat before you go drinking.

Maybe I was the only one who knew what the rules were. There I was in the middle of the night, standing in an empty living room, with an empty bottle of IPA in my hands, which were covered in powdered sugar. Where the hell did everyone go?

To bed, you idiot. Where you should be. Tee time’s at 8 in the morning.

So there I was, in a panama hat at Churchill Downs. Sophisticated. Refined.

There you were with that hat, which had a cute black bow in the back, clearly made for a woman, fitting perfectly on your head.

billys bbq

And there I was, sliding into oblivion at a bar in Lexington after California Chrome won the second leg in its bid for the Triple Crown. Thanks to a little help from Makers Mark and Woodford, we skipped dinner to make the start of the Kentucky Derby, only to find ourselves guzzling beers and bourbon before putting down our first bit of food at about 10 p.m. I paid for $20 worth of songs from a jukebox and continually pressed the wrong button – what I thought was Johnny Cash was actually Miley Cyrus, over and over again.

I remember watching the Kings-Ducks game, not quite comprehending why hockey was being played in Kentucky, then realizing that I was just watching the game on TV.

And there I was, sitting cross-legged on the sidewalk in front of our vacation rental, my spirits sagging just before 18 holes, wondering when we were coming back again.

So yeah, I had a good time.


About Chairman Mao

I like fomenting socialist revolutions and purging my homeland of pseudo-intellectualism and capitalist dogma. I also like sports, dogs and food (although I wouldn't consider myself a foodie).
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