Kentucky Bourbon Trail Trip 2022

I’m fresh off the dopest of trips and excited to share so much of it with you:

In April, a colleague of mine decided that she wanted to celebrate her husband’s birthday with a trip to the Kentucky Bourbon Trail for him and 10 friends. She asked The Black Bourbon Guy to craft a can’t-miss itinerary for the group, including the best and most interesting distilleries, restaurants, and bottle shops we could find. The coolest part? I would be going and leading the group!

The Kentucky Bourbon Trail is an amazing place to learn about the history of bourbon and to taste some of the best bourbons in the world. Beginning in Louisville, the Trail is made up of just over 40 different distilleries on the official Trail, and many others that are not officially recognized, each with its own unique story and style of Bourbon. There are a few things to keep in mind if you ever plan to visit. Here’s a great beginner’s guide for a successful trip to the Kentucky Bourbon Trail.

Our journey started with a Tuesday 5:50 am flight from Raleigh, a connection in DC, and finally landing in Louisville just in time to rush to Old Forester for the only tour spot we could manage at what is unquestionably my favorite distillery. We squeezed in some day trips to Frankfort and Bardstown, and event saw some twilight racing at historic Churchill Downs racetrack. Our journey came to an end on Sunday at 10:00 pm, when we touched back down at RDU. The middle was filled with some amazing stops and stories. Here are some of the highlights:

Buffalo Trace Distillery
Frankfort, KY

Home to some of the titans of whiskey: EH Taylor, Elmer T Lee, George T Stagg and many others

Obviously one of the most popular and well-known distilleries in the world. Given how popular they are, it can be hard to land a tour at Buffalo Trace. If you are willing to put in the effort, I promise you the juice is worth the squeeze. We scored some spots on the Trace Tour, which showcased some of the most historic buildings on the property, including the historic Warehouse C, which had its roof torn off by a tornado in 2006. Bottles of EH Taylor that survived the storm have been sold for as much as $15,000 on the secondary market.

If you’re willing to show up early, the distillery releases a special bottle each day at 9am. If you’re lucky, you can score a bottle of EH Taylor Small Batch, Weller Special Reserve or Blanton’s, all at MSRP. Worst case scenario, they’ve always got standard Buffalo Trace for sale. The bourbon gods smiled upon us and we managed to grab some Weller and EH Taylor. 

Old Forester Distillery
Louisville, KY

Located in the heart of downtown louisville's historic whiskey row

There are two rules for choosing your favorite bourbon: 1. You can find it. 2. You can afford it.

For both of those reasons, Old Forester is my favorite distillery, hands down. While I missed our tour due to flight issues, we had a great time at their amazing Downtown Louisville facility, featuring their gorgeous 44-foot-tall copper column still “Big Penny”. Word is, the tour was excellent. As one of the oldest continually operating brands on the Kentucky Bourbon Trail, Old Forester has so many great stories to tell. You also get the opportunity to char a barrel, yourself, as you tour the facility.

The Old Forester Bar has some fun cocktails and offers flights of one of my all-time favorite bourbons, Old Forester Birthday Bourbon — a limited-edition yearly release, honoring the birthday of their founder, George Garvin Brown. We happily spent way too much time and money here, and I look forward to making visit.

Heaven Hill Bourbon Experience
Bardstown, KY

Crafting some of the best brands in American Whiskey, since 1935

Another must-see stop on the tour. While most of their distilling is done in Louisville, Heaven Hill ages all of its products on its enormous campus in Bardstown. We got the hook up from a colleague and scored a spot at the Whiskey Connoisseur Experience here. It started with a quick, yet immersive video experience, located inside the Distillery Theater,  which was designed to look like the inside of a bourbon barrel. Next up, was a fun tasting of some of their available premium options, including Elijah Craig Toasted Barrel and a selection from their Parker’s Heritage series. The best part? They reserved a premium bottle for each of us at the end.

Castle & Key Distillery
Frankfort, KY

The OG destination for bourbon tourism, located in Kentucky's capitol city

Opened in 1887 by Colonel EH Taylor, himself, Castle & Key sits on the site of the historic Old Taylor Distillery. These cats are fermenting and distilling spirits inside a real-life castle; it was amazing to see the operation. They’ve been selling vodka and gin for a while now, but their small batch just hit the market and sold out with the quickness. In addition to the castle, the property also features beautiful sunken gardens, a moat, a limestone springhouse, and an enormous, ivy-adorned barrel-aging warehouse that doubles as a nuclear fallout center, in case of emergency. Definitely would not be the worst place to spend the last of your days.

Preservation Distillery
Bardstown, KY

Because bigger doesn't always mean better

Preservation Distillery is a hidden gem on the Kentucky Bourbon Trail. Located in historic Bardstown, Kentucky, their proprietary bourbon is still aging and not quite mature enough to bottle, but they have a handful of unique whiskey blends on the market. Each of their offerings is pot distilled in small batches of 1-3 barrels.  While most of the operations that we visited are titans in the industry, which makes touring a smaller, up-and-coming spot like Preservation a great opportunity to get a little closer to the process. Also, fewer employees mean that everyone knows the business from top to bottom. Definitely a great stop.

Woodford Reserve Distillery
Versailles, KY

Locals will be quick to remind you that it's pronounced "vər-SAYLZ", unlike its French predecessor

Since we’d already taken a trip to Churchill Downs, it was only right that we visit the official sponsor of the Kentucky Derby. Woodford distillery is one of the most famous stops on the bourbon trail. The picturesque site overlooking the Kentucky River is worth the drive alone, but their bar allows you to taste some of the best bourbons you can find. We stopped here for some bourbon, cheese, and chocolate on their back porch, which overlooks several beautiful horse pastures.

Willett Distillery
Bardstown, KY

Lunch at the Willett bar is a can't-miss experience

I intentionally saved the best for last here. Built in 1936, Willett Distillery is one of the most recognized names in the whiskey world – Their Family Estate Bottled Bourbons are some of the rarest bottles around. As famous as they are for their whiskey, someone told me that they take their food program just as seriously.  Fortunately for us, that turned out to be some amazing advice.

The Bar at Willett has some great décor, and is decorated with a bucket list of their releases. Their menu is made up of shareable small plates, showcasing the creativity of their culinary team. We tore through almost the entire menu and ordered a couple items twice. Their tempura-battered broccoli and seared octopus served with chimichurri atop house-made hummus were two of my favorites.

And then there were the drinks. We needed a slight break from drinking straight whiskey, and Willett’s cocktail game was certainly up to the task. They advertise their whiskey sour as being “life-changing”. While it’s not quite there, it is amazing to watch them chill their coupe glasses with dry ice, while making sours. They also stamp some of their large ice cubes with the Willett logo. Pretty dope.

Proof on Main @ 21c

A Restaurant In A Hotel, Not A Hotel Restaurant

If you’re a fan of delicious, locally-sourced seasonal menus, than Proof is the place for you. A great friend of mine is the Chef de Cuisine at Proof, and dude is an extremely talented individual. We had an amazing dinner on Friday night, featuring some amazing food, drinks, and top-notch service. It doesn’t hurt that there’s a gorgeous modern art gallery around the corner for you to check out before or after dinner. 

This truly was the ultimate Kentucky Bourbon Trail experience. We had memorable distillery trips, the perfect blend of activities, and scored some great bottles and souvenirs along the way. We even managed to visit the historic Churchill Downs, site of the Kentucky Derby. It was a great way to celebrate a birthday in style!

Interested in your own guided trip to the trail?

Cheers!

The Black Bourbon Guy