2 Days On The Kentucky Bourbon Trail (Complete Local’s Guide)

The Kentucky Bourbon Trail is a great destination I think everyone should visit at least once. With so many amazing distilleries in the region, it’s no wonder it can feel overwhelming to plan your perfect route. Especially if you only have a couple of days. That’s why I put together this 2-day Kentucky Bourbon Trail itinerary to help you make the most of your time.

From big names like Maker’s Mark and Woodford Reserve to smaller craft spots, there’s no shortage of memorable stops. As someone who grew up in Kentucky—and even got married at Buffalo Trace—I know a thing or two about visiting the Bourbon Trail. I’ve spent years exploring the region and helping others do the same, always discovering new favorites along the way.

Whether it’s your first visit or a return trip, this guide will walk you through the top distilleries, great places to eat, and helpful tips to make your experience smooth and memorable.

Happy travels to Kentucky!

Just a quick note: This page might include affiliate links. If you click and purchase anything from the links I receive a tiny commission to support this website. The good news? I only recommend products I actually use and believe in. So you’re getting the best products at a super good price.

Moxy Louisville

A Marriott hotel, the Moxy Louisville Downtown is located right off Whiskey Row within walking distance of many of the downtown Louisville distilleries. The best part about the Moxy is it can be really affordable for its location, costing as little as $110 a night.

21c Hotel Louisville

One of my favorite hotel chains, the 21c is part art museum and part modern hotel. The Louisville 21c is located near the Louisville Slugger Museum and Factory and is a great location for shopping and dining.

The Grady

The Grady stands out for its character and historic charm, making it an ideal choice for travelers seeking a more intimate experience. Its location allows for easy walking access to downtown distilleries, ensuring you can indulge in the bourbon trail while enjoying the hotel’s unique ambiance.

You could also choose to stay in Shelbyville, which is full of unique places to stay on the Bourbon Trail, and just a 30 minute drive from downtown Louisville.

For more on where to stay on the Bourbon Trail be sure to check out my complete guide! 

Kentucky Bourbon Trail in 2-Days: Complete Itinerary

This 2-day Bourbon Trail itinerary is built for those seeking both urban distilleries and the Kentucky countryside. You’ll find a blend of Louisville’s famous Whiskey Row as well as select experiences in Bardstown as well as a stop at Jim Beam, too

It’s designed so that you can mix and match, but if you want more suggestions do check out my 3-day itinerary. This guide will give you more helpful ideas to make the most out of your trip on the Kentucky bourbon Trail.

And if you want a more complete guide, with helpful cost, tour, and other information, don’t miss my complete guide to visiting the Bourbon Trail.

Day 1: Visiting Louisville’s Best Distilleries

Starting in Louisville it makes sense to spend Day 1 visiting distilleries in the area. Most of the distilleries now operate at least visitor experiences on Whiskey Row downtown, but there is so much more than Whiskey Row to discover!

Want to Skip the Bourbon Trail Guesswork?
My Booking Blueprint includes the exact booking windows, best tours to choose, sample 1-day routes, and food & drink stops from a Kentucky local.

Morning in Louisville

Start your day with breakfast at Wild Eggs. This local chain is popular for breakfast and brunch with dishes like Kelsey’s KY Brown (a breakfast twist on the Kentucky Hot Brown) worth the visit. Take it from my own experience, breakfast before a full day of distillery tours and tastings is a must.

I love Stitzel-Weller because it’s a working bourbon distillery with rickhouses in Louisville, and it’s the only place to see such operations without venturing at least 30 minutes outside of town. Join the Stitzel-Weller’s Experience tour and learn about the history of bourbon within Louisville. The tour takes you through some incredible history that will set you up for the rest of your Bourbon Trail journey.

By contrast, Rabbit Hole is a modern distillery looking at innovative ways to craft bourbon. Their facilities are modern, they offer a cocktail at the start of your tour (what a perk!), and they have the best gift shop of any of the distilleries. The Rabbit Hole Distillery Tour is well worth your time. 

Afternoon On Whiskey Row

With two distilleries down, take a rest and load up with lunch at one of the many downtown favorites. Against the Grain (within walking distance of Rabbit Hole!) has a great selection of pub food and local beers on draft. If you want something a little more upscale, Porch Kitchen and Bar creates unique Kentucky southern food with favorites like shrimp and grits and fried chicken.

Of all the tours to do on Whiskey Row, Old Forester is the best. Their Old Forester Tour provides a glimpse at the entire bourbon making process, has a great tasting experience, and gives you access to products you can’t find on the shelves. 

By now, if you’re like me, you’re probably toured out. So spend the last part of your day doing something else. Some options include: Bourbon & Billets offers unique blending experiences to give you the ability to literally craft your own bourbon.

Or if you’re a foodie consider booking a NULU food tour. Louisville is also home to some incredible museums, like the Muhammad Ali Center and Slugger Museum & Factory

Travel Tip! If you want to bring home some special bourbons, visit Justins’ House of Bourbon for the best selection in Louisville. You’ll likely pay a premium here but if you want hard-to-find items, this is the place.

If you want a truly Louisville dinner experience, reserve a table at the Brown Hotel and try the original Kentucky Hot Brown. It’s a classic dish that everyone needs to try when visiting Kentucky.

After dinner if you’re up for another bourbon experience (you’re on the trail so of course you are) visit the legendary Watch Hill Proper for a drink. This restaurant and bar is where master distillers, distillery owners, and other industry leaders snag pours of exclusive bourbons (but also great cocktails). 

Trying to Plan Your Own Route? My Booking Blueprint gives you themed 1-day itineraries, food recs, and booking help, all for less than the price of a cocktail.

Day 2: Exploring Bardstown And Beyond

I don’t think you can fully get the entire Bourbon Trail experience by just visiting Whiskey Row and the Louisville distilleries. What I think really sets the trail apart from other experiences is seeing and experiencing bourbon where it’s done: rural areas, mostly on the Kentucky River. 

So today we’re headed out of town! Renting a car (if you don’t have one) is the easiest way to get around but you can book a tour instead. Personally, I think going with a tour group is super expensive and doesn’t add to your experience. The DIY method is what works best (and will save you hundreds of dollars).

Renting a car? Be sure to check out my guide to saving money on car rentals!

Morning In Bardstown

Take the 55 minute drive from downtown Louisville to Bardstown, Kentucky. Bardstown is home to many of the best distilleries, including Lux Row, Willet, Heaven Hill, and Bardstown Bourbon Co. 

Heaven Hill has some of the most unique tours on the market. I recommend exploring their list and picking what sounds most interesting to you. The You Do Bourbon experience, where you can taste premium products and bottle your own, and Bottled-in-Bond tours are both excellent choices. 

Bardstown Bourbon Company is one of the coolest experiences you can have in bourbon.I recommend their Rickhouse Barrel Thieving experience, for only $30 it’s a steal and so unique.

After your thieving tour be sure to snag lunch reservations in their amazing restaurant and bar. They serve upscale Kentucky classics like a fried chicken sandwich and bread pudding.

Afternoon On The bourbon Trail

After spending your morning in Bardstown, head to Jim Beam in Loretto on your way back to Louisville. Beam has a lot of great tour options but their standard tour is hard to beat. It includes an “open bar” concept tasting experience, which allows you to taste their premium products.

Beam certainly has a more formal approach to their tours but they are still worth it. Be sure to consider travel time between Bardstown and the Jim Beam distillery. I suggest a 3:00 or later tour time.

After your last stop on the Bourbon Trail, make yourself dinner reservations at one of my more recent favorite restaurants, The Village Anchor. This local establishment is a bit off-the-beaten-path and will be a uniquely local experience.

The Village Anchor serves up many southern classics, but their Kentucky hot brown is my favorite. Here they also have a wide selection of bourbons on the menu. (Their old fashioned is perfection.)

If you’re up for it, after dinner take to one of the speakeasies in Louisville. Personally, I’m partial to The Black Rabbit. But if you want something down on Whiskey Row try Hell or High Water.

Other Ways To Spend 2 Days On The Bourbon Trail

Of course, there are plenty of distilleries to choose from when visiting Kentucky. And there are numerous ways to spend 2 days on the Bourbon Trail, too. This itinerary is just one suggestion based on what I’d tell my friends as a Kentucky native.

But here are some ways you could adapt your itinerary:

Explore Central Kentucky

Instead of spending a day in Bardstown you could choose to enjoy Central Kentucky’s distilleries. Here you’ll find Buffalo Trace, Woodford Reserve, Four Roses and more. You could opt to drive from Louisville or choose to stay in Frankfort instead.

It’s full of some of the best bourbon distilleries you can visit but it’ is a bit further than it’s hard to visit both Bardstown and the area without missing out on Louisville’s Whiskey Row, so you likely need to choose one or the other.

Spend Your Time In Louisville

If you don’t want to rent a car you can instead choose to only opt for Louisville’s nearby bourbon distilleries. Here you’ll find famous distilleries like Old Forester and new-age distilleries like Rabbit Hole and Angel’s Envy, too.

Many distilleries in the greater-Kentucky area now offer tasting room experiences in Louisville to accommodate people who can’t travel beyond as well. And though these aren’t the same as enjoying the sites and smells of a rickhouse in the Kentucky countryside, it’s an easier way to spend two days on the Kentucky Bourbon Trail if you don’t want to rent a car.

More Kentucky Bourbon Trail Tips and Inspiration

I hope you enjoy the Kentucky Bourbon Trail as much as I do! Be sure to check out these other stories to help you plan your visit:

• Here’s your complete guide to visiting the Bourbon Trail, which includes plenty of helpful tips and tricks to visiting all in one easy place.
• Don’t forget to find a place to stay – I’ve compiled all my favorites in this helpful guide!
• Have more time? Check out my 3-day trail itinerary with some more ideas on visiting.