Louisville, I Think I Love You

OK, love may be a strong word, but I am certainly in strong like with Louisville, Kentucky. I wasn’t sure what to expect from my first foray on the Bourbon Trail, and I am happy to report that Louisville is pretty darn adorable.

We drove down from Chicago and stayed in the Phoenix Hill neighborhood, which was a historic German immigrant stronghold. It has since gone through a number of different lives and rich communities and is now weathering gentrification. Some of the blocks have a rougher exterior but don’t be put off, the neighborhood has a fantastic arts scene, small businesses, and some good eats (always my primary concern). Most importantly, it is centrally located.

Our first stop was Angel’s Envy (literally, we crossed the bridge into Kentucky and drove directly to the distillery because we were running late for our 4pm tour). This small batch distillery has been run by three generations of the same family. I tried a lot of bourbon over the course of our trip, and this was one of my favorites. Despite the heat, the tour was delightful, and our guide answered every question, which isn’t easy to do when you are traveling with two PhDs in chemistry. Located near Louisville Slugger Field, the distillery has a fun history as it is built on an old race track…for goats! 

Pro Tip: The Bourbon Trail runs all over the state and you need several days to do it all. Each section has things to see along the way, so avoid cramming too many tastings into each day so you can stop and explore in between tours.

Angel’s Envy’s copper stills are integral to the making of bourbon. They help remove sulfurs and other impurities from the brew.

Billy Goat Strut feels like it should be the name of a bourbon.

Next, we checked into our adorable shotgun house for the weekend. I have to note that the couple we rented from were more thoughtful and welcoming than just about anywhere else I have ever stayed in my entire life.

Anyway, since it was a friend’s birthday, we did a quick change and made a dash over to the River House Restaurant and Raw Bar. While the food is wonderful (nom cheesy grits) it is nothing compared to the view. It does get busy, so call ahead to see if you can get a seat on the patio overlooking the Ohio River. Sipping a cocktail and watching the barges meander by is just about the most relaxing thing you can do in Kentucky.

River House Louisville

The tail-end of the sunset on the River House patio.

The following day we took on the northern bit of the Bourbon Trail, just outside of Lexington. The drive out is more beautiful than any picture can do justice, and our driver, Ray, was fantastic enough to point out the can’t miss landmarks as we made our way through the hills. My hat goes off to him. He had 30 years of driving experience and an encyclopedic knowledge of every stable each Kentucky Derby winner is housed in along the route. He even explained how the fencing works for each stable; double-ed up fencing so the horses don’t jump it; white fence means old, usually massive farm, or just a farm with a lot of money because white paint needs to be redone more frequently; black fence means newer. As it turns out, those horses live better than the majority of Americans and after listening to Ray talk about it, I seriously considered trying to rent a stable in Lexington (it has to be cheaper than my place in the Bay Area!).

We hit four distilleries on the way: 

  • Woodford: This distillery is as beautiful as its bourbon. Gorgeous, rolling hills and imposing old stone buildings, Woodford makes you feel like you have stepped back in time, or onto the set of a Kentucky-based Peaky Blinders. The site itself is a historic landmark, first distilled upon in 1812. We happened to stop by while they were cleaning those fabulous copper stills, a rare treat for science nerds like us!
  • Four Roses: No longer your grandma’s trash bourbon, Four Roses was recently purchased by Kirin Brewery Company, Ltd. from Japan, and they are not playing around. The bourbon we tried was good stuff.
  • Wild Turkey: The place looked like bourbon prison. The view from the tasting room was beautiful, but the buildings where they make and house the bourbon look and feel miserable. I spent the entire time wanting to shout “free the bourbon!” and am convinced this is why their bourbon tastes like a shoe mixed with nail polish remover. Store a liquor with hate, and it will treat you with hate on the way down.
  • Town Branch: This was my favorite distillery/brewery. The staff spent extra time answering our various questions on Kentucky liquor taxing structures, and the chemistry behind distilling. They also brew beer and had all kinds of things for us to try. Their beers were just as good as their bourbon, and they make a scotch inspired beverage that is delicious. Needless to say, I want to go back ASAP.

Pro Tip: Hire a car if you plan to do multiple tastings and/or tours. While the distilleries are not pouring with a heavy hand, bourbon can sneak up on you and DUIs are not cool.

Bonus Pro Tip: You need to book distillery tours/tastings in advance and come with closed toed shoes to avoid a safety lecture. These are working distilleries, after all (says the group who only brought sandals because they looked better with our outfits…).

Tucked in the hills and surrounded by ancient trees, Woodford feels like peaking back in time.

According to our guide, polishing the outside of a still is something distilleries do infrequently, so it was lucky we caught the crew in action!

Bourbon jail, where Wild Turkey sends its bourbon to be punished.

After Ray got us back to the shotgun house safe and sound, we headed over to the Holy Grale. This whimsical spot is located on the trendy end of Baxter Avenue at Bardstown Road. Built in 1905 in an old church, the place does a great job of paying homage to its history, with just the right amount of irreverence. The staff knows their menu well and is super familiar with their beers. I recommend asking them what to try on tap, and you won’t be disappointed. The food is the real star of the place, with some delightful and surprising combinations. We tried all of the specials — even the carrots were good!

Next, we went in search of live music and found it exactly three doors away at O’Shea’s. A standard Irish pub, we still had a great time, thanks in large part to the band that I heckled endlessly. In my defense, they were asking for requests, so I just kept yelling whatever song I wanted to hear. Maybe Loretta Lynn wasn’t what they were expecting, but it’s what they got. Eventually, they invited me on stage and I took the opportunity to melt faces off the poor, unsuspecting patrons with some opera. Thanks, college, and bourbon! (I know video exists, but I boggled the order of the words, so I am not showing it to anyone, ever). My equally rowdy friends even made a mad dash for the tables closest to the stage, so the poor band had to deal with us all night. All I can say is, Blaze and Cody, I hope the crowds at your next gig were equally enthusiastic. 

Pro Tip: You can get all of your favorite bourbons in Louisville for about $6 (rocks or neat), which is almost play money compared to the astronomical amount we pay in California. Take my advice, the serving size is not pretending, so don’t get carried away! Similarly, there are some fantastic local beers. Enjoy them, and take a cab/lyft wherever you decide to go!

The Choir Loft is the darkly lite gem of the Holy Grale, have a bite up there for heading to the patio

The evenings in Louisville are perfection, and the Holy Grale knows that. Just don’t forget bug spray, those mosquitoes are serious.

O’Shea’s aka the bar in which I heckled a band until they let me sing opera. Quality bourbon choices.

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