3-Days on the Kentucky Bourbon Trail

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Advisor - Robert Love
Curated By

Robert Love

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A waterfall in a green landscape in Kentucky.
Curator’s statement

If you are a fan of Bourbon, or whiskey in general, I highly recommend taking a long weekend and enjoying the Kentucky Bourbon Trail. This is a one of a kind, mini road trip adventure. (Keep in mind, transportation is available. Drink responsibly!) I found my love for whiskey in Ireland when I toured the Jameson Distillery. I was amazed by the process from start to finish and realized there is a lot more that goes into distilling than you would imagine. Understanding this, it led me into researching the rich Bourbon history in the US. From that, I found the Kentucky Bourbon Trail! This guide will take you through 3-full days of Bourbon adventures. Pro Tip: A lot of the locations in this guide are close don Sunday. So use Sunday as a travel day... or recovery day, I'm not judging.

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Day 1: Exploring Louisville

Kentucky whiskey bottle in nature.

For your first full day on the trail, I highly recommend spending the entire day in and around Louisville. Pro Tip: Several of these places are within walking distance from each other. Take liberty to rearrange the best route from your hotel.

Start your day out with a stop at Butchertown Bakery to fuel up. Make sure you grab a few Cruffins (Crescent / Muffin Hybrid) because you will need the carbs.

Most distilleries in town open up around 10, and you have a full day ahead of you. So let's get started. First stop is Angel's Envy for the one-hour Signature Tour. After you wrap up here, "hop" or walk on over to Rabbit Hole Distillery. This is such a modern take on all of the distilleries you will visit on this adventure. Make sure you get a little nip of the Heigold, their high-rye bourbon.

Now that we have two stops under our belt, its time to grab some lunch. I recommend grabbing some BBQ at Doc Crow's.

With a full belly, walk down W Main to the Evan Williams Bourbon Experience. Pro Tip: Make sure you ask if they have any flavors that aren't in stores. From here you can round out the afternoon at Old Forester Distillery.

By this point, if you aren't ready for bed... make your way to Sidebar at Whiskey Row. At this point in the day, I am ready for a big burger and fries.

Day 2: Distillery tour - East to Lexington

A wooden whiskey tasting room and chairs.

Today is going to be a little different. On day one we were based in Louisville and stayed centrally located. Today will be traveling East to Lexington, with stops along the way. That said, make sure you have a designated driver or arrange private transportation.

Start your day by grabbing a quick bite at Please & Thank You before heading to Shelbyville. When you roll into town, your first distillery stop of the day is Bulleit Distilling Co. While here, make sure you sample their pre-made Old Fashioned cocktail. Pro Tip: Don't arrive too early, they currently do not open until 10:30am.

Once you finish up at Bulliet, we are off the Frankfort for lunch at Bourbon on Main. After lunch head out to Buffalo Trace Distillery, not only for the Bourbon, but for the scenery. This is such a beautiful location rich with history. The next stop in Frankfort is Castle and Key Distillery. Here you can try their Restoration Rye Whiskey and their small batch Wheated Bourbon.

Now its time to head on over to your final destination, Lexington. When you get in town, grab a bite to eat at the OBC Kitchen and get ready for your last full day.

Day 3: Last day at Bourbon Trail

Wooden whiskey barrels.

No matter what you decide to do today, you need to start with breakfast at DV8 Kitchen. Did someone say cinnamon rolls? First stop today, you can stick around Lexington and visit James E Prepper Distillery and taste their award winning 1776 Bourbon and Rye. After this, you will head to Bourbon on Rye for lunch.

Moving on, this afternoon can be a "make your own" adventure day. If you are up for driving again, you can find several distilleries within about a 20 mile range. Two that I would highly recommend are Four Roses Distillery and Wild Turkey. If you work the timing out, you can knock these both out in one loop and be back in time for dinner.

For your last night on the Bourbon Trail, you should make it a point to get reservations for Old Bourbon Country Kitchen. OBC Kitchen is a chef-driven restaurants and bourbon bar located in the heart of Lexington. This is the perfect way to wrap up 3 packed days of adventure in Kentucky.

Need to Know

For more travel tips, check out Fora Advisor Bijoy Ahah's guide 4-Day Itinerary for the Ultimate Louisville Bachelor Party.

Advisor - Robert Love

Travel Advisor

Robert Love

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