The Urban Bourbon Trail

We were told that from our doorstep in Lexington Kentucky we could easily visit four legendary bourbon distilleries in two days. That’s swell, and all, but we figured we’d cover far more ground in under an hour by making a single stop to Lexington’s Bluegrass Tavern. With 209 bourbons on their menu, ranging in price from $4 per glass to ‘don’t ask,’ Bluegrass was the perfect place to introduce ourselves to Kentucky’s amber elixir.

There are few pleasures in life more satisfying than sipping a good single-malt Scotch while nibbling some authentic toffee shortbread. To get our attention, Kentucky’s rot-gut needed to compete with the best of Scotland. Knowing very little about bourbon, I was reserving judgment, but my expectations weren’t high.

I looked at the bourbon menu and for all I knew it was written in Greek. I recognized Makers Mark and Wild Turkey. I knew they were fine for brining pork chops and making mint juleps but I wanted something good enough to drink straight up, and to find that, I needed some help.

The bartender instructed us to narrow down a price range and from there he’d steer us in the right direction. We pointed toward the lower right hand corner of the menu where the more expensive brands were listed, but away from those in the ‘don’t ask’ category. We’re not pikers, after all, but neither are we interested in discovering a great bourbon that is too expensive for mere mortals to drink.

He first poured us a ‘wee dram’ (sorry, it’s hard not to think of Scotland when I think of whiskey) of Vintage 17, and supplied us with some ice and a bowl of Hershey’s Kisses. “Trust me” he said, about the kisses. The Vintage 17 went down smooth, with a taste of sweet toasted brown sugar. It’s a nice whiskey, but it’s missing the smoke, peat and complexity I love so much in Scotch. A bite of the milk chocolate brought out more of the flavor in a surprising way. Maybe chocolate is to bourbon what shortbread is to Scotch.

Rowans Creek, and Wathens were up next. The Wathens was even smoother with a bit more complexity than the others. This was a liquor I could find a place for in my cabinet. But it was the Old Rip Van Winkle 107 proof that blew us away. It was like an explosion of flavor: vanilla, caramel and oak. The stronger than average alcohol content was so well balanced that all you noticed was the slow, lingering, warming sensation as it worked its way to your toes. We had to get a bottle.

And that is where the trouble started.

We visited probably half a dozen liquor stores, both large and small, in search of a souvenir bottle to occupy a prized place next to our beloved Oban. The only thing we got for our efforts were bemused smiles from store owners who were far better acquainted with the particular wild goose we perused.

Little did we know that the Van Winkle family operates its distillery under a strategy of deliberate scarcity. Like any luxury product, the demand for premium bourbon is highly cyclical. Many small producers get into trouble by ramping up production to meet demand in the good times, only to be left high and dry when bad times inevitably arrive. To avoid that fate, the Van Winkle’s deliberately limit supply of their libations to create an almost permanent shortage. If you’re lucky enough to be one of the limited bars, restaurants, or family friends on their distribution list, it isn’t much of a problem. Every one else is shit out of liquor.

We arrived in Kentucky looking to learn something about the State’s signature drink. What we acquired instead was a White Whale that we’ll pursue until the end of our days. No longer can we see a liquor store or bar shelf without asking about Old Rip. Most folks outside of Lexington have no idea what we’re talking about. That’s okay. We know she’s out there.