Road Trip from Chicago to Kentucky Bourbon Trail

Why Kentucky Bourbon Trail, KY?
As famous American writer William Faulkner said, “Civilization begins with distillation“.

For any bourbon connoisseur pondering over an ever impending bucket list trip to Kentucky Bourbon Trail with their best buddies, two words – Do It! It is totally worth the hype AND a lot more. You will create a ton of memory dividends for life. 

Quick 101Kentucky Bourbon Trail is a program to promote bourbon whiskey in Kentucky – it represents several top Bourbon distilleries dispersed mainly around three cities – Cincinnati, Louisville and Lexington. 

Barrel Tasting Station at Bardstown Bourbon

How to Plan your visit?

• Choose your cities and the distilleries. There are 18 signature and 24 craft distilleries spread across the state. For those with limited time, we would recommend concentrating on the highlighted area around Louisville which has most *signature* distilleries. Here is the sacred map:

You will find the official version at KBT

We stayed at Louisville downtown and did following tours in a day –

Rickhouse Barrel Thieving Tour at Bardstown Bourbon Co, Bardstown. 
Makers Mark Tour at Makers Mark, Loretto.

Noteworthy mentions:
Four Roses is widely acclaimed for its alluring, Spanish-style distillery.
Wild Turkey is located atop the rolling hills, giving you an incredible view of the ravishing KY River. 

Special thanks to Lori for above suggestions.

Aerial view of Four Roses distillery 

Here is the listing of all signature and craft distilleries.

• Run through this indispensable emergency checklist.

• Run through the tech essentials to turbo-charge your road trips.

Our Road Trip from Naperville

November 12-14, 2021

Road Trip
Naperville to Louisville, KY.
320 miles, GPS ETA was 5 hours, we made it in 7 hours with many breaks.

We stayed at a single family home in the East Market District at Louisville, also called Nulu (New Louisville) via Airbnb.  Our house is currently off listing but you could try out many others here.

abnb_houseOne of the more popular houses in Nulu, listed at Airbnb

Day 1 – The Whiskey Tours

Bardstown Bourbon Company Tour
More info on the Rickhouse Barrel Thieving Experience here.
Set your GPS here.

What better way to kick-start the tour than Bardstown, the bourbon capital of the world.

Our first stop was a one-of-a-kind whiskey thieving experience tour at an actual rickhouse. Bardstown Bourbon Company is one of the newer distilleries and made a stellar impression in every way – the tours, the slick modern amenities, the eatery and the ambience. If you are looking for a blend of modern and authentic Bourbon experience, this is a must-visit brewery. 

On a murky, chilly day which was perfect for whiskey tasting, we ambled over to the rickhouse.


Here’s how a rickhouse looks like.

Barrels being aged (Bardstown Bourbon)

Once inside, we were greeted with enormous ricks holding the barrels in a temperature controlled environment. And our host patiently explained about the distilling process. It was fascinating to know terms like Devil’s Cut and Whiskey Thief!


Using whiskey thief to extract the spirit from the barrel(Bardstown Bourbon)

The Bardstown whiskey, as we drank straight out of the barrel, was bold and strong. The coalition of many different whiskeys was delectable.

We got the signature Bardstown Bourbon whiskey glass as the souvenir

The visitor lounge area was swanky.

Company of great friends and bourbon

After taking a few swigs of the Fusion series and dawdling to our heart’s content, we headed over to the eating area.

The food and the drinks both were sumptuous.


Nothing beats having Old Fashioned at the Bourbon Capital of the World.


Our bellies full and minds unruffled, we lounged at the large outdoor sitting area.

Heated outdoor sitting area (Bardstown Bourbon)

The entire experience was as warm as this creative heating grill.


Makers Mark Tour at Star Hill Farm Provision
More info on the classic Makers Mark Tour here.
Set your GPS here.

On our way from Bardstown to Loretto (short 30-minute drive), you will relish the Kentucky backroads. There were bourbon related fabrications all around.

A Jim Beam photo op out of nowhere

Makers Mark Tour was at the historical Star Hill Farms Provisions site.


Star Hill Farms Provisions is a sprawling facility with a dash of history, the latest additions include a premium fast-casual restaurant.

Courtesy: Makers Mark

We strolled through the paved track – the tour encompassed both indoor and outdoor activities.


Being mid-November, weather was not too chilly, making it a very soothing hike.


There were still remnants of the fall foliage.


The entire property was rich in creative props.



Makers Mark was all about tradition and history.


After a brief on the Makers Mark history, we headed over to the temperature controlled rickhouse.

PXL_20211113_200716399 (2)

And finally, we had the much-awaited guided whiskey tasting session. 

Elaborate whiskey tasting spread at Makers Mark

We capped off the tour with the souvenir section where we enjoyed the DIY stall to put the signature red wet wax seal on our Makers Mark bottle.

The patented signature red wax seal of Makers Mark

The Evening Saunter at Nulu (New Louisville)

After a quick pit stop at home, we got ready for a boys night out. Our first stop was at 8up, a drinkery and casual dining restaurant.

Outdoor seating at 8UP

We moseyed up on the Nulu area post the dinner. 

Nulu is voted as one of the best eating neighborhoods in the nation. Other than the culinary prowess, it is abundant in specialty stores, art galleries and antique shops.

Not every day you see an all-season ping-pong table like above

Check here for all the attractions at Nulu

Day 2 – Activities and Journey Back Home

Kentucky Derby Museum is minutes away from the downtown and highly recommended before your ride back home.

Courtesy: Derby Museum

Churchill Downs racetrack is another not-to-be-missed Kentucky gem. Known for its highly acclaimed Kentucky Derby, you can time your visit to hit the Fall season of the races. 

Courtesy: Kentucky Derby

Ride Back Home

And 7 hours and a few pit stops later, we were back in Chicagoland.

So long, Kentucky Bourbon Trail!

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2 thoughts on “Road Trip from Chicago to Kentucky Bourbon Trail

  1. The photography is amazing and the colors are vibran. I also appreciated that ping pong table- never seen an all-weather one like that. Looks like a great adventure.

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