Day 1 on the Bourbon Trail

Breakfast at Wild Eggs

Like the good planners we are, we had all our restaurants picked ahead of time! This allowed us to make the most of our trip and not sit around looking for a nearby place to eat. Our first breakfast was at Wild Eggs, about a 5 minute walk from the hotel and another 5 minutes to our 11 a.m. tour at Angel's Envy. This ended up being about a 15 minute walk because I forgot to bring my vitamins with me to breakfast, but thankfully we had enough time in between and Rachel was a great sport about it. Safe to say we got our 10,000 steps quickly on this trip!

Tour at Angel’s Envy

Of all the distilleries we planned to see, Angel’s Envy was our first choice. It did NOT disappoint. A 15 out of 10, go there and take a tour. It was one of my favorite distilleries from the whole trip.

We arrived 15 minutes early as instructed by our tickets and browsed the gift shop as we waited. The Bourbon Trail has a field guide booklet of all the distilleries on the trail. As you visit each one, you get the distillery page stamped and dated. Some also give out a free gift or a discount. From Angel’s Envy, we received a pin. I didn’t know how much bourbon I’d end up liking on the tour or bringing home. This ended up being the perfect souvenir and I’m eager to complete the book!

Important note: the field guide is sold at all the distilleries on the trail and at the Derby Museum. HOWEVER, I noticed it was the least expensive at Angel’s Envy, for $6.35 after tax (as of writing) and ranged from $10 to $15+ everywhere else. It is also available for purchase on the bourbon trail website.

As I shared before, this was one of our best tours mostly due to our guide, Logan. He taught us so much and the tasting at the end of the tour was the most engaging. Ask for him when you visit. The tour began with a discussion of what makes an alcohol a bourbon. He explained the history of the distillery, why Louisville has the best water for bourbon (hint: it’s the limestone aquifer!), their distillation and aging process, and the labeling process. There is no standard definition for what is considered a small batch and it varies from distillery to distillery. Angel’s Envy bottles and labels about 20,000-25,000 bottles per 24 hours. The incredible part? These are labeled and checked for quality by hand. Talk about a labor of love.

Also on the tour, we learned about the heads, hearts, and tails of the distillation process. The head is unpleasant tasting (also probably dangerous to consume) and very high in alcohol content, such as methanol and esters. The hearts are the alcohol we drink, and the tail is disposed of. This helps explain why distilleries were able to pivot and produce hand sanitizer during the early days of the Covid-19 pandemic - they were already producing a hand sanitizer like liquid as a byproduct of distillation. All they had to do was add a few ingredients to create a different product.

The tour concluded with a tasting and it was without a doubt the most informative tasting of the trip. We learned how to properly taste bourbon (more on that below) and the impact water/ice has when you’re drinking it. It was this tour and tasting that took me from “yeah, I like bourbon” to “YES! I drink bourbon.”

Overall, we were there from 45-minute to an hour. All the tours we participated in had a similar tour structure, but they really are such different experiences.

TALK TO ME. WHAT MAKES A BOURBON?

A bourbon needs to be:

  • made in the United States

  • 51% corn

  • distilled to no more than 160 proof

  • barreled at no more than 125 proof

  • aged for at least two years in new charred oak barrels

  • bottled at least at 80 proof

HOW TO TASTE BOURBON

  • Observe the color. Usually the darker the color, the heavier the taste.

  • Stick your nose in the glass and leave your mouth slightly open. Inhale. No need to be polite and delicately inhale. Stick your nose in the glass.

  • Take a small sip and swish it around in your mouth. Called the Kentucky chew, this acclimates your mouth to the drink. Swallow it and note the taste.

    • Did you feel the warmth radiate in your chest as you drank the bourbon? This is called a Kentucky hug!

  • Take another sip and compare how it tastes to the first sip. Is it the same? Different flavor notes?

  • Now try it with a few drops of water, and I mean a few literal drops. Some tours gave us eye droppers to do so. You can skip the acclimating step. How does it taste?

Trying bourbon with and without water was critical. There were some I didn’t care for neat and had I not known this water tip, I would’ve passed on the bourbon altogether!

If there is one thing I learned during this whole trip that sums it up in one sentence, it would be: Water is to bourbon what air is to wine.

HAPPIEST COWS IN AMERICA

Several of the distilleries we went to, including Angel’s Envy, sell or gift their spent grains to farms as cow feed. This leads to what they call the happiest cows in America.

HOW ANGEL’S ENVY GOT ITS NAME

For every five years a barrel is aged, about 30-40% of the bourbon is lost to evaporation. This is referred to as the angel’s share. Therefore, what is leftover is the Angel’s Envy. Finally, any bourbon that is absorbed by the wood in the barrel is called the devil’s share. And now you know a factor as to why bourbon can be pricey - it’s lost to evaporation!

Lunch at Naive Kitchen + Bar

Following the tour, we went back to the hotel so I could drop off the bottles and goodies purchased at the distillery. We then made our way to lunch and had a nice time walking to Naive Kitchen + Bar. The restaurant is about a 10 minute walk from the distillery. They describe themselves as “veggie forward” and there are enough options for both plant based and omnivore eaters on the menu.

As Rachel and I walked through the neighborhoods, we kept looking up! There are many murals painted high on the buildings, adding literal color to the city. I took a picture of one that summed up our trip together.

Tour at Rabbit Hole

Now having food in our stomachs, we walked another 10 minutes to Rabbit Hole. This distillery we didn’t know much about and selected it due to its proximity to the hotel and their tour availability.

This tour was different from our first one. We began the tour with a small glass of bourbon and our guide, Terry, shared that Kentucky makes over 90% of the world’s bourbon, with 30% of that coming from Jefferson County (where we were!). Unlike larger distilleries, Rabbit Hole doesn’t have a master distiller. Honestly, I didn’t think this would matter but when we concluded with the tasting, I acknowledged the difference in tastes and finishes, and didn’t like it. More on this in a bit.

This distillery is another small batch distillery, producing about 3800 bottles per day. Remember, “small batch” refers to how many bottles can be produced in a day rather than the size of the company and there is no standard definition.

The distillery has great visuals on the walls to really help conceptualize the distillation process. We learned more about how wood is burned, and malt is used to change a flavor or release an enzyme. They also use some of the spent grains from the previous batch in their next batch, as well as feeding it to cows. We were able to see the tanks with the yeast bubbling up, and the room smelled of warm oats. Terry is the one who taught us that water is to whiskey what air is to wine. Wheat makes a bourbon sweet whereas rye adds a spice.

The tour ended with a tasting, and surprisingly I didn’t enjoy any of the liquors we sampled. I had read their description online and it sounded up my alley. Buy after trying the various bourbons both with and without water, I still didn’t like them. Regardless, I’m glad we visited the distillery and the tour was worthwhile.

Copper & Kings

Realizing how much time we had left in the day, Rachel booked us a tour at Copper & Kings while we were still sitting at bar in Rabbit Hole. We had found this distillery in our planning and it was different from them all as it’s for American brandy! I couldn’t figure out why Rachel was so eager to go there. Turns out she hadn’t realized this and we enjoyed a good laugh. We then walked from Rabbit Hole in the NuLu area to Copper & Kings in Butchertown, about a 15 minute stroll. On the way, we found an adorable store called Jones & Daughters that had opened earlier that week and made note to return before we left as Rachel wanted to purchase a bourbon print.

This distillery was a good break from the two we visited earlier in the day. The stills are different in shape, pot stills vs column stills, which produce smaller batches than the bourbon distilleries. Lastly, grapes are the base in brandy. Funnily, they were distilling apple brandy the day we visited.

We visited the basement where the brandy is aged and I heard music playing. Odd as it’s a basement and people aren’t down there for long periods of time. The guide explained that they use sonic aging to age the brandy. This is where the base beats agitate the alcohol. Had we not stopped by, we wouldn’t have learned about this! The tasting at the conclusion of the tour had options for brandy, gins and other liqueurs. It was a nice sampling, but I didn’t love anything enough to take it home. I always appreciate tastings because you’re able to form a connection with a product and learn how to properly pick up on flavors.

Dinner at The Post

By now, we had seen a lot, drank a lot, and walked a lot. It was now time to freshen up at the hotel and put on additional warm layers before the evening activities. We took a rideshare to The Post for a pizza dinner. It was delicious. I somehow ate the entire pizza. I was that hungry! Not only was the pizza yummy, I liked how local the restaurant is. I didn’t feel like we dined at a restaurant that caters to visitors. I would recommend you visit!

Old Louisville Ghost Tour

Our last activity for the day was an Old Louisville Ghost Tour. We originally planned to do this about 9:30 p.m. and increase the spooky factor, but needed to reschedule as that tour guide was sick. The tour operator was very accommodating and communicative about this change. Plus now knowing how cold it was and how much we walked during the day, it ended up being better for us to take the 7:30 p.m. walking tour.

The walking tour was about a 2 hour loop of Old Louisville with stops at about 10 locations with haunted histories. We heard stories of a ghosts and claims of ghostly sightings, dating back to the 1940s. We also heard current day horrors, such as a house where bodies were found in the basement and is ongoing trial. Our guide, Angelique, was an animated story teller. Some of the stories were lengthier than others, but she kept our attention and successfully led our group of about 15 people.

None of the stories were so traumatizing that I had trouble sleeping. It was fairly tame. When booking the tour, I anticipated stories that focused around the history of the city with ghostly aspects, such as, “The general in this battle died here and his ghost is seen still leading soldiers.” This was not that type of tour, and instead relied more on word of mouth. Overall, it was a good tour. I’m both relieved and bummed we did not see any ghosts walking around.


Wow! Such a long day. Thank you for making it to the end of this post. Day 2 is the Derby Museum and another distillery tour. If you want to support my travel blog or you can’t wait for all the posts, you can buy a digital download of our itinerary here. This 3-night Louisville itinerary includes the hotel, distillery tours, Churchill Downs, and restaurant recommendations.

USABrandi AkermanComment