Bourbon Trail (Lexington/Louisville) 2024!
This was a trip a couple of years in the making! Between schedules, parenthood, and work stuff, it kept getting pushed back. But come August of 2024, we finally made it happen!
I’ve always been curious about bourbon. I’ve had it a few times, but never really knew much about it. So, i figured, I’ll learn by diving head first, and visiting the bourbon homeland, Kentucky! I put a poll out to a group of friends that I thought might be interested in this type of thing, and my buddy Jon and cousin Suren signed up to join me!
This trip had two components that I wanted to pull together. Firstly, I wanted to check out the Bourbon Trail, but I also wanted to do a long motorcycle road trip. So I figured this was a great opportunity for both! From Baltimore, our destination in Kentucky was 8 highway hours, or 12 scenic twisty road hours away. But as the weekend approached, Hurricane Debbie made her way up to coast. It was just went rainy weather by the time it made its way between Baltimore and Lexington, but still not something I’d want to be on a motorcycle for 12 hours for! But luckily, I’ve got my beloved 2008 Mustang GT California Special in the garage ready to give me plenty of twisty road enjoyment, out of the weather! I’m truly lucky to have the driveway that I have, and don’t take it for granted!
The Plan!
Ok, onto the trip planning! The Bourbon Trail is broken up into separate regions. Not knowing if this would be our first of many Bourbon Trail visits, or first and last, we decided for the first round we’ll visit the home of some of the major distilleries that we were familiar with, out of the Lexington/Louisville region. With the first decision made, we got down to planning our itinerary for the weekend!
We gave ourselves a long weekend for the trip, arriving in town Friday evening, doing tours Saturday and Sunday, then leaving to head home on Monday. There are a few ways to tackle creating an itinerary. The easy button for planning is to book a trip with one of the many tour companies. They take the guesswork out of picking distilleries, and finding times, calculating distances, etc. It also gave folks an easy answer to being careful about driving after having consumed alcohol. We chose to create our own itinerary, however, so that we could specifically choose which distilleries we wanted to visit, and control our day a bit more. We would be mindful of our alcohol consumption, and our ability to drive. With 3 drivers, and plenty of time between distilleries, and staying hydrated, we could manage just fine!
Doing it this way takes a bit of logistical planning. The best path we found was to open the scheduler page for each distillery we were interested in in a separate tab, along with Google’s MyMaps tool, and start drawing out a route, and then referencing the scheduler for each distillery to give ourselves enough time for the tour, to have a break, eat, and then drive to the next distillery. As long as you’re systematic about it and start putting the pieces together, it’s not that hard. But it can be daunting to find a place to start. So I would suggest picking the distilleries you’re interested in, then mapping, then scheduling. You’ll find that you will need to tweak and adjust based on tour times, but that’s easy to do once you start putting things together! Tours vary in price between 20 and 40 dollars roughly per person.
For our visit, we decided for Saturday we’d do Wilderness Trail, Castle & Key, Woodford Reserve, and James E Pepper. For Sunday we’d do a bit of a slower schedule, only planning for Whiskey Thief and Angel’s Envy in Louisville. We had attempted to fit in Buffalo Trace, but their scheduling system was a real pain. It was a moving window system, and you had to wait to make the reservation the second it opened. Both Jon and I attempted to do it, and within seconds of the window opening, all of the slots were booked up. We suspect it’s tour operators that are taking them all. We got onto the waitlist, but we got a message that there were openings available just a couple of days before the trip, and our schedule had already been locked in.
The Journey!
So when trip time came around Jon offered that we do an overnight at his cabin out in Lost River, WV. It was a great idea, especially given that with the weather, it was a long slog getting out of the DC/MD/VA area. It also meant that my 12 hour scenic tour through WV would only be about 8 hours, since the other 3 would have been spent getting to the cabin, which was perfectly located on the way.
After staying at his amazing cabin, I took off in the morning on the scenic route, and Jon took a more direct route. The aforementioned storm did a bit of a number on the southern route through WV, with plenty of tree debris and gravel wash out all over the roads. I was still able to enjoy some of the most beautiful roads that Appalacia has to offer, outside of the popular and well known Skyline Drive and Blue Ridge Parkway.
These roads were tucked away, in very rural WV, and I rarely saw anyone for the entirety of the drive from Lost River to Flatwoods WV, where I got back onto the highway to make good time getting to Lexington.
All right, now that we’ve covered one big part of the trip, the journey, lets get to the destination part, the Bourbon Trail! After we all arrived at our AirBnB in Frankfort, we ventured out into downtown Frankfort to grab dinner. We found a cool place called The Brown Barrel, that had some great food and drinks, and primed us for our upcoming adventures!
Bourbon Time!
Wilderness Trail Distillery
The next morning, we geared up and drove over to Wilderness Trail. This distillery was a bit south of Frankfort, and as we headed down we started getting into some beautiful rolling hills, arriving at Wilderness Trail. Wilderness Trail took a very science based approach to their tour, walking through the technical aspects of bourbon, and how flavors and character enter the processes. It was a great, low key tour, and the three of us were the only people on the first tour. At the end, we had our tastings, a Yellow Label Straight Wheated Bourbon, Black Label High Rye Bourbon, Green Label Rye Whiskey, and Barrel Pick of the Day (cask strength rye). I really liked the first one, it was nice and smooth, and easy to drink.
Castle & Key Distillery
The next distillery was Castle & Key, and this was a much different vibe. There was a sizeable group, and the tour had less of a rural distillery feel and more of a distillery complex feel. It was in the old original buildings, which was super cool. One distinct difference was that Castle & Key also makes a Gin, and they showed us the pot still that they use for that, which was super cool. Castle & Key has a really interesting history, being passed around, shutting down for prohibition, then partially dismantled, and then stood back up transitioning from the Old Taylor Distillery to the modern Castle & Key Distillery. For the tasting Small Batch Bourbon Whiskey, the Restoration Rye Whiskey, and the Rise Seasonal Gin, mixed into a cocktail. I liked the Small Batch Bourbon Whiskey, but was really blown a way by the Gin cocktail! It was really enjoyable. After the tour, we had a bit of a break to have lunch before Woodford, and decided to grab some street tacos from a taco truck on site at Castle & Key. They were incredible, and did a great job filling us in prep for our next tour!
Woodford Reserve
Our next stop was Woodford Reserve. Another level of modernity and refinement from a tour experience from Castle & Key, the grounds that the distillery sits on is an interesting blend of old buildings, and modern processes. The visitor center and shop were ultra modern, with exquisite displays and a ton of bourbon derived products, from chocolates to teriyaki sauces, to bbq sauces. It was a fun tour, involving a tour bus ride, and ending in a fancy tasting hall. The tour guide was fun as well, lacing in personal anecdotes and stories with her description of the process. The tasting was fun, and our first that was paired with a bourbon infused chocolate. This tasting also featured the biggest spread, their Bourbon Whiskey, Malt Whiskey, Rye Whiskey, Wheat Whiskey, and their Double Oaked Bourbon. All of their offerings were great, with my favorite being the Double Oaked and the Wheat Whiskey.
James E Pepper Distillery
This was our last distillery for the day, taking us into downtown Lexington. This was an interesting setup, more of a party vibe complex than rural distillery of the others. The complex has the distillery in the middle, surrounded by restaurants, ice cream shops, and outdoor seating. We arrived early for our tour, and were offered some Old Fashioneds while we waited (that we had to pay for haha). This honestly was the best Old Fashioned I’ve ever had, and I quickly learned why. At the start of the tour, we were told that James E Pepper himself, along with his mixologist invented the cocktail in the early 1900’s. This claim seems to be roundly debunked by other historical accounts, but nonetheless, there’s probably a bit of truth to aspects, including the specific recipe used, which is a bit different from modern Old Fashioneds, so even if they didn’t invent it, they put their mark on it, and we got to have one, in the way it was made 100 years ago, and it was delightful! The tour was similar to the others outside of that romp through history, with the distillery being closed and reopened sporadically, before opening in its current state. The tastings were good, Bottled in Bond Bourbon and Bottled in Bond Rye, although not as good as some of the others we’ve had throughout the day. Certainly pleasant though. Probably the best from James E Pepper was what they let us taste after in the bar, their Decanter Barrel Proof Bourbon. Jon and Suren couldn’t resist getting a bottle for themselves. After that, we went to this awesome pizza place next door, and upstairs we found a pool table where we could hang out for a while. After that we wrapped up and headed back to the house. That wrapped up an awesome day, and left us looking forward to Sunday!
Whiskey Thief Distilling
On Sunday we had a bit of a later start, which was good for us, given the busy Saturday we had. After breakfast, we headed over, and were met with a distinctly different feel from any of the other distilleries that we’ve been to. This was a small craft distillery, with a single barn for the distilling, and a second for storage. After a short tour, we got to the tasting, which unlike the other experiences, was the longest tasting session of the trip so far! This is because their tasting setup was 5 barrels laid out, based on aging window, proof, and mash bill variety. They had 4 bourbons, and 1 rye whiskey. To get a tasting, one of the hosts used a “Whiskey Thief”, essentially a long straw, to take some out of the barrel itself, and they poured it into our glasses. And they were letting us have as much as we wanted, of any kind, and they just kept pouring! Of all of us, our favorite was barrel number 3, a 6 year, 69% corn, 21% rye, and 10% malted barley mix, at 110 proof. We all decided to get a bottle for ourselves, and for another cool factor, we got to bottle our own our own bourbon, after which they attached the labels and seal. On top of that, Whiskey Thief isn’t something I can buy locally, and definitely not one I can bottle myself! So I figured this would be the one to bring home. We had fun pouring our own bottles (with most of the bourbon making it inside of the bottles!), and then headed towards Louisville to prep for our final tour of the weekend, Angel’s Envy.
Angels Envy
This was our last tour, in the heart of Louisville. Similar to Woodford Reserve, but on a slightly smaller scale, their gift shop and facility was super nice and modern. We went through the now familiar processes, touring the stills and fermentation tanks, but were also treated to a new experience, their bottling facility! They do their own bottling onsite, and the equipment was really cool to look at. The tasting session was very nice as well, with a cool assortment of bourbons, with their Port Cask finished Bourbon, and Rye Whiskey finished in Caribbean Rum Casks. A third bourbon was offered, a distiller select, what was aged longer. They were all great, my favorite being the standard port cask bourbon and the distiller select bourbon. All in all, a great experience and tour!
Wrap up and Homeward Bound!
After Angel’s Envy, we grabbed some amazing food at a Cuban place in Louisville, La Bodeguita De Mima Cuban Restaurant and Rum Bar. After that, we took Suren to the airport, and went back to the house to rest up for our drive home on Monday.
As for the drive home, it was a relaxed uneventful drive via highway back home. Driving through the Appalachians is always incredible, even on the highway. After about 8 hours on the road, I got back home, and unwound from the trip. It was also an amazing opportunity to spend time with Jon and Suren, and they made would would have been a good weekend amazing! It was a great experience, and I would love to do it again in the future!
