The Perfect Kentucky Bourbon Trail 2 Day Itinerary (2025)

Looking for the best weekend getaway itinerary on the Kentucky Bourbon Trail?

The Kentucky Bourbon Trail is an official designation of the bourbon distilleries in the areas of Frankfort, Lexington, and Louisville, Kentucky.

There are currently 45+ distilleries on the trail, so it would easily take 2 weeks to experience them all, so I’ve compiled a list of the best ones to visit if you’re short on time.

My main criteria included brand popularity, history, and aesthetics of the property and tasting.

I have also included some additional activities, restaurants, and places to stay when enjoying your time on the Kentucky Bourbon Trail.

Kentucky Bourbon Trail 2 Day Itinerary

I will start by saying that I am by no means a bourbon expert or connoisseur.

I’ve really only had it when my husband orders an Old Fashioned for dinner and I drink the last few sips that have been watered down.

So I created this itinerary based off of brands that I’ve heard of before, distilleries that actually had tours available on the days we were visiting, crowdsourcing recommendations from friends, and making sure to include the aesthetically pleasing distilleries purely because I just enjoy places that look nice.

Additionally, distilleries with unique experiences or elements to their tours or tastings were also factored in.

I confirmed with my husband which distilleries I had narrowed down our list to, so it is approved by an actual bourbon drinker.

Here is the exact itinerary we followed when we spent 2 days on the Kentucky Bourbon Trail.

The night before, we drove down from Dayton, Ohio and stayed in Simpsonville, Kentucky, which is about halfway between Louisville and Frankfort, so we could be close to our first tasting the next morning.

On day one, we toured Bulleit, Castle & Key, and Woodford Reserve.

Then we had dinner in Frankfort, visited Daniel Boone’s grave since it was right there, and did a pirate themed escape room in town.

We also stayed at a hotel in Frankfort that night.

On day two, we toured Four Roses, Maker’s Mark, and Old Forester.

We finished the day with dinner in Louisville, walking around town, and then driving back home to Dayton, Ohio.

Below are the details about each distillery’s tour and tasting experience, the foods we recommend in the area, and the best places to stay on the Kentucky Bourbon Trail.

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Kentucky Bourbon Trail Day 1: Frankfort

Since we were driving ourselves the entire time, we limited ourselves to 3 tastings a day, though you could potentially fit in 4 if you pick places that are close to each other.

You can see in the image below that we started in the West, then gradually made our way toward Frankfort by the end of the day.

Bulleit Distilling Co. Bourbon Tasting

Our very first tasting was at Bulleit.

We did the Unlocking The Senses tasting at 11:30 am, which is a 30 minute experience.

They have an option that includes a tour for just $5 more, but because of the times available for the distilleries we were visiting, we wouldn’t have had the time.

At the time of our visit, it was $20 per person for our tasting.

What was unique about this tasting is that they really used all the senses – sight, sound, taste, touch, and smell.

Throughout the tasting, each bourbon had a scent box that was paired with it and the lights and sounds would change throughout the experience.

You’ll get to taste 4 different styles of whiskey that they produce and my personal favorite here was the rye whiskey.

Castle & Key

Castle & Key is one that I hadn’t heard of before, but when I saw the property, I knew we’d just have to go, and my husband agreed.

This one is about 30 minutes away from Bulleit, so we booked our tour and tasting for 1 pm to give us enough buffer time in-between experiences.

We booked The Distillery Experience, which is a 1 hour tour followed by a tasting.

At the time that we visited, it was $30 per person.

The unique element here is obviously the history and beauty of this property.

But they also offered a gin cocktail during their tasting that I enjoyed and I actually bought the bottle of gin from the gift shop afterwards – it’s called the Rise Seasonal Gin.

They also give you a piece of chocolate to have with your tasting!

I know this is supposed to be the Kentucky Bourbon Trail, but once again, my favorite whiskey of theirs was the rye whiskey.

Woodford Reserve

Woodford Reserve was our next distillery, less than 10 minutes away from Castle & Key, so we were able to book a tour for 2:30 pm and have enough time in-between to get there.

I picked this one because it is the main one that my husband drinks, but that’s mostly because that’s what most restaurants that we go to offer in their Old Fashioned cocktail.

We did the Path To Flavor tour and tasting, which is a 70 minute experience, that also includes a shuttle bus to take you around the property.

What I liked about this tour and tasting is that it was $32 per person, but only $25 for the designated driver that wouldn’t be drinking.

The highlight of the tour was their historic Still Room and the barrel storage warehouses.

This tasting had 5 different styles of whiskey and it also came with a piece of chocolate.

Another unique element of this tasting is that there are tasting cards for each whiskey that you’re able to take home with you.

Once again, my favorite was the rye whiskey, but I actually also enjoyed the double oaked whiskey.

Dinner: Bourbon On Main

From Woodford Reserve, downtown Frankfort is about a 20 minute drive.

We didn’t have a particular place in mind, but figured we would just drive downtown and park and see what caught our eye.

I also tried to do a little research online on the way to see if any places stood out.

We ultimately decided to have an early dinner at Bourbon on Main because of the historic element of the restaurant.

There were 3 of us on this trip, so we ordered quite a bit of food.

For our first appetizer, we shared a pretzel with beer cheese dip and celery.

Then we shared deviled eggs with pork belly and pickled onions.

For our meal, my husband had the house burger, which came with bacon preserves, a fried egg, gouda, lettuce, onion, tomato, and pickles.

Then I had a side of mac n cheese, which I don’t currently see on their menu, but it might have been one of their daily specials.

In the background of the photo, you’ll also see that the 3rd person with us had a taco quesadilla.

For dessert, we shared a chocolate chip bread pudding.

Daniel Boone’s Gravesite

This may seem like a super random thing to add to this itinerary, but the cemetery is right in downtown Frankfort and you’ll likely see signs for it all over.

But the reason we decided to stop is that Daniel Boone is actual my great-uncle, through my grandad’s side of the family!

9 generations back, Daniel Boone’s sister, Sara, is my great-grandmother.

If for no other reason, at least check it out because it sits on a hilltop with a phenomenal view below.

It’s completely free and takes maybe 10-15 minutes of your day.

Capital Escape & Axe Throwing

On the other side of town is an escape room, which is one of my favorite activities to do when I travel.

Especially when they are locally owned and not part of a national brand that I could experience anywhere.

We did a pirate themed room and we were able to escape with just 4 minutes to spare!

This one had a lot of unique elements we hadn’t experienced in other escape rooms before.

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Kentucky Bourbon Trail Day 2: Louisville

After day 1, we stayed at a hotel in Frankfort, where our day ended.

Day 2 requires a bit more driving, but because we could only visit 6 distilleries on this trip, we had to pick the ones at the very top of our list.

Four Roses Distillery

Our first tasting for day 2 was Four Roses Distillery, which was about 30 minutes from Frankfort.

We did the Taste of History experience, which was a 30 minute tasting with no tour.

It was one of the cheapest tastings at just $16 per person.

This one I had picked based off of the look of the label, the popularity of the whiskey’s themselves, and the architecture of the property.

It looks like a Spanish villa.

This tasting included 4 different whiskeys.

We purchased a bottle of their Single Barrel Bourbon because it was our favorite AND because it was awarded the World’s Best Single Barrel Bourbon by the World Whiskies Awards.

Maker’s Mark

Our next bourbon stop was Maker’s Mark, which is about an hour away from Four Roses.

I picked this one because it’s easily one of the most famous, most popular, and most recognizable.

We booked the Shutdown Maker’s Mark Tour for 12:30 pm.

At the time of our visit, it was $24 per person and it’s a 1 hour tour and tasting.

I was pleasantly surprised by the aesthetics of the property.

It reminded me of Norway at Epcot more than anything else.

My least favorite part of this experience was that this was the only distillery where we weren’t allowed to share our tastings.

Because I was the driver, I would just have a small sip of each one, then my husband would drink the rest.

But Maker’s Mark said that it wasn’t allowed and there were actually several other couples that were annoyed by that too because it’s just wasteful.

Our tour guide, to be honest, was kind of on the grumpy side the whole time, and just rubbed a lot of people the wrong way.

But, a highlight of this tour is seeing the assembly line where the whiskey is bottled and seeing the iconic red seal being dipped onto the bottles.

You can add on to your experience and dip your own bottle to take home, but we did not splurge for it on this trip.

Old Forester Distilling Co.

Our final stop was Old Forester Distilling Co. in downtown Louisville.

It’s about an hour and 15 minutes from Maker’s Mark, so it’s quite a long drive.

We booked the Old Forester Tour for 3:45 pm, which combines a tour with a tasting.

It’s a 75 minute experience for $32 per person.

I booked this one because of the name recognition and because of its location on Whiskey Row in Louisville.

A unique element of this tour is being able to set a whiskey barrel on fire!

Old Forester was another tasting experience that included a piece of chocolate, which is probably my favorite perk of all of these tastings.

Our favorite was the 1910 Old Fine Whisky 93 Proof, so we purchased a bottle of that one to bring home.

Dinner: Merle’s Whiskey Kitchen

It was about 5 pm when we finished our last distillery tour and tasting, so we decided to take a stroll down Whiskey Row to find a place to eat dinner.

Merle’s Whiskey Kitchen stuck out to us the most as being a popular, local place, at an affordable price.

We tried a little bit of everything from fried chicken to mac n cheese to cornbread to green beans to mashed potatoes and gravy.

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Where To Stay On The Kentucky Bourbon Trail

Our itinerary was a little bit of a road trip around the entire Kentucky Bourbon Trail.

Depending on how much you’re wanting to drive, you may want to stay in one hotel the whole time or move around.

These are all the hotels we’ve stayed in when we’ve visited the area and recommend for your visit.

Hampton Inn Simpsonville

Hampton Inn Simpsonville is in-between Frankfort and Louisville.

We stayed here the night before our first day of whiskey tastings because we were driving down from Dayton, Ohio and wanted to stay somewhere affordable, but as close as possible to our first destination.

We love Hampton Inn because they have free parking and free breakfast.

Click Here To Book Your Hampton Inn Simpsonville Stay Today!

Home2 Suites By Hilton Frankfort

Home2 Suites By Hilton Frankfort is obviously in Frankfort.

We stayed here after the first day of our whiskey tastings.

It’s not in the center of downtown, but still nearby.

Home2 Suites also offers free parking and free breakfast.

It’s a newer brand for Hilton that caters to a younger crowd, but the rooms are set up for work-stays and longer stays.

Click Here To Book Your Home2 Suites By Hilton Frankfort Stay Today!

Doubletree Suites By Hilton Hotel Lexington

Doubletree Suites By Hilton Hotel Lexington is my favorite of all the hotels in the area, but it wasn’t near any of the places we were visiting on this particular trip, but it could be a good starting or ending point for you depending on where you’re traveling from or to.

It’s designed in the style of the local distilleries but also for the Kentucky Derby.

You just have to watch the video to get an idea of just how nice this hotel is!

Click Here To Book Your Doubletree Suites By Hilton Hotel Lexington Stay Today!

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Conclusion: Kentucky Bourbon Trail 2 Day Itinerary

There are plenty of other distilleries to visit on the Kentucky Bourbon Trail and definitely some high profile ones that we missed, but when you’re limited on time, you have to prioritize!

I enjoyed every single place that we visited.

They each had unique elements to their tours and tastings and I especially loved the aesthetics of each one.

We’ll definitely be back in the future to visit even more!

It’ll take 6 more weekend getaways to tour them all, lol.

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