Two Day Itinerary for the Louisville Urban Bourbon Trail

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The last time you spent two full days drinking, you were probably in college. Or maybe your life is just way more interesting than mine. But the Urban Bourbon Trail in Louisville gives you the chance to relive that time in your life when you were able to drink for an entire weekend without worrying about Monday morning.

Jason and I are both lovers of Bourbon. I assume since you’re here that you are too. And there’s no better place to drink bourbon than in Kentucky. When we originally started thinking about our Bourbon-fueled trip to Kentucky, we looked into exploring the distilleries that are spread all throughout the state. But since we were limited to a weekend, we turned to Louisville instead for more options in a smaller radius. We wanted to try as many places as possible without having to worry about driving to our next destination.

In fact, we drove to Louisville, but didn’t use our car once while we were there. We called for a ride a couple times, but for the most part, everything was within walking distance! It allowed us to have a perfectly worry-free weekend of eating, drinking, and having a good time without having to worry about how we were going to get back to the hotel.

The Louisville Urban Bourbon Trail

Louisville’s Urban Bourbon Trail is great for first time visitors to get acquainted with the city. Our first stop in Louisville was to their visitor’s center to pick up our Urban Bourbon Trail passports. From that moment on, we were determined to collect our six stamps, earn our Urban Bourbon Trail t-shirts, and taste as much of Louisville as possible.

If you’re ready to take on the Urban Bourbon Challenge, check out these stops to earn your stamps:

Urban Bourbon Trail Stop #1: Sway

Sway is a hotel lobby bar that is very close to the Visitor’s Center. It was the perfect first stop of the day. The bartender was very kind (and non-judgemental about how early we were getting started on drinking cocktails.) She was proud of her city and happy that the Urban Bourbon Trail brought us in to visit.

We ordered a drink called a Bourbon Berry (Jim Beam Black, muddled strawberries, bitters, and ginger ale) and the Sway Signature Old Fashioned. We were very happy with both choices.

Detour From the Trail: The Jim Beam Urban Stillhouse

We had originally planned for this to be our first stop, but we got started too early and they weren’t open yet. While this isn’t an official stop on the Urban Bourbon Trail, we needed to make a stop here. Visiting Louisville for the first time and not seeing the Urban Stillhouse would be like going to New York City and not seeing the Statue of Liberty. If you’re going to be a good tourist, you’ve got to see it.

Once the Jim Beam Urban Stillhouse opened their doors, we signed up for our tasting. This facility is set up as more of a gift shop than an actual distillery, which is perfectly fine by us. They have a guided tasting where guests get to sample four of their bourbons (including one you get to pick yourself) and learn more about the history, the flavor, and the company. Jim Beam’s Distillery is on our list of places to visit in the near future. We love Jim Beam, and we were plenty happy to poke around at merchandise and bottle our very own bottle of Urban Stillhouse Bourbon.

We loved the Bottle-Your-Own experience because it was a fun way to get introduced to their bottling process (including their distribution hurdles) from start to finish. And at the end we had a very unique gift to take home.

Detour: Old Forester

At this stop on the Louisville Urban Bourbon Trail, you’ll pay a $10 cover charge to get into their tasting room. A cost that is well worth the price because each entry comes with your choice of either a cocktail or a bourbon flight. We wanted to try as many different kinds of Bourbons as possible during our trip, so we chose to get two bourbon flights.

Old Forester Statesman was by far our favorite bourbon, but we got to try practically everything on their roster. It was fun being able to try out the tasting techniques we learned on our guided Jim Beam tasting as we attempted to pick out the distinct flavors in each bourbon before deciding on our favorites.

Stop #2: Haymarket Whiskey Bar

One of the requirements in order for a bar to be featured on the Urban Bourbon Trail is that they must have at least fifty (yes, five-zero!) bourbons on their drink menu. While Haymarket should be best described as a dive bar, there is absolutely no shortage of bourbon here. It’s unlikely that there’s a bourbon they don’t have. While there was a slight musty smell in the air, Haymarket was also full of heart. There were locals enjoying a drink at the bar, the bar tender was incredibly friendly and we had a great time playing “I spy that bourbon” as we gazed at their massive selection of bottles lined up at the bar.

Haymarket’s charm is less about atmosphere and more about the expansive selection. This bar gives you the rare opportunity to try something you’ve never seen before.

Detour: Rabbit Hole

While this stop won’t count towards your Urban Bourbon Trail passport, you should consider catching a ride over to the “NuLu” district (that’s short for “New Louisville”) to see how a craft distillery operates in Louisville. There is no portion of the distilling process that is kept a secret here. You will learn about making bourbon every step of the way. In fact, they even let you reach your hands into the still and take a taste. Don’t worry about germs, the alcohol burns that all up. At least that’s what they told us. I took a taste of bourbon every single step of the way. It was such a unique experience and I would highly recommend this tour to anyone who is curious to learn more about the process.

At the end of the tour, you’ll again be lead on a guided tasting of their bourbon. The flavor is much different than the other bourbon’s you’ve tried thus far. It will be much heavier on the spicy rye flavors. I also loved that at the very end they handed out post cards and I was able to write post cards to my friends that they mailed for us!

Stop #3: Garage Bar

Not only was this a stop on the Louisville Urban Bourbon Trail but it also came as a recommendation to us from a friend from Louisville. Garage Bar was within walking distance of Rabbit Hole, and it was the perfect place to grab dinner. On a Saturday evening, this place was absolutely packed. I’m convinced we got the last available table in this huge space. There were so many people inside, but we didn’t have to wait to be seated.

Maybe it was the fact that we were drinking all day, but their margherita pizza absolutely hit the spot! I loved their house cocktails, District 8, made with bourbon, orange juice, tonic, bitters, and lemon.

Stop #4: Merle’s Whiskey Kitchen

If I could travel back in time, I would have visited this restaurant earlier and I would have made this our stop for lunch and dinner. Merle’s Whiskey Kitchen was our absolute favorite stop. Their drinks were delicious, and their parmesan garlic fries were divine. The next time we’re in Louisville, we’re going to work this place into our agenda. You don’t want to miss it!

Stop #5: O’Shea’s Public House

We made a late night stop at O’Shea’s because we were having so much fun on the Urban Bourbon Trail. However, I wasn’t too thrilled about visiting O’Shea’s. I can’t say how the rest of the evening had looked for them, but when we arrived at 9:30pm, the place was pretty empty. We grabbed a seat at the bar and the bar tender seemed pretty impatient that we didn’t immediately know which drink we wanted to order. I asked her for a cocktail menu, and that seemed to annoy her even more. If we were staying in Louisville longer than the weekend, I probably wouldn’t have even asked for her to stamp our books.

Twelve hours earlier, when we were drinking cocktails at 9:30am, the bartender was welcoming us to Kentucky, crafting drinks without judgements, and was more than happy to stamp our passport books. I typically don’t feel comfortable “looking like a tourist” and I was so happy that this bartender from Sway put me at ease. But at 9:30pm that same day, I felt ashamed to even ask for a stamp for fear of looking like a “tourist.”

I was very happy with our drinks here, but not so thrilled with the experience. I hope this one unpleasant encounter is not an accurate reflection of this pub, but because of our experience, I don’t recommend this stop.

Stop #6: Corner Bar & Restaurant

Determined to not end our evening on such a sour note, we decided to stop at yet another bar to have a more positive final stop of the night. We ended up at Corner Bar, another hotel lobby bar that really gives your typical hotel lobby a run for their money. This was a cool place to hang out. While we sat at the bar (for fear of falling asleep) there were large comfy chairs that many people had burrowed into. There were also pool tables, and the TVs were playing the “funny home videos” type clips which lead to some interesting conversations with neighbors.

I had their Signature Old Fashioned, and Jason sipped on Woodford Reserve. We were very happy to have ended our night here. But after visiting nine bourbon destinations, we were ready to head back to our hotel.

You can learn more about our hotel and other hotels I’d recommend in Louisville on my post How to Spend Two Perfect Days in Louisville.

Detour: Stitzel-Weller Distillery

If you are in the mood for starting a second passport on this trip, you could grab your copy of the Kentucky Bourbon Trail Passport and collect a stamp at the Stitzel-Weller Distillery. But if you’d rather not start another passport, this place is still worth the stop! If you had no idea there were two different passports, you can also read about those on my post mentioned above: How to Spend Two Perfect Days in Louisville.

The Stitzel-Weller Distillery is home to a few different brands of bourbons, but most notably, Bulleit calls Stitzel-Weller home. It was interesting to compare this facility to Rabbit Hole and get the opportunity to take in the differences in their two operations. Unlike Rabbit Hole, Stitzel-Weller doesn’t appear to do any fermentation on site, but they do age all their bourbons in the massive rackhouse.

This incredibly informative tour also finishes with a guided tasting, and will leave you with a sudden urge to learn even more about Bourbon’s History.

If you’re looking for a quick read that will teach you more about the history of Bourbon, check out this book: Kentucky Bourbon Whiskey: An American Heritage, by Michael R. Veach.

Detour: The Evan Williams Bourbon Experience

The name of this stop is enough to get you curious, isn’t it. “What is a bourbon experience and how do I get one?” This tour is more of an interactive history lesson than a distillery tour. Lucky for us, we both love learning about history and we very much enjoyed this tour. If you’re looking for an authentic distillery experience, this isn’t it. An added surprise on this tour was that we were able to taste a sample of “New Make,” which is bourbon fresh off the still before it is aged. Coming in at 125 proof, this was worse than drinking rubbing alcohol. That was kind of their point in allowing you to taste a sample though. So much of what makes a bourbon happens in the aging process.

The end of this tour finishes with another guided tasting. Our guide on this tour was very enthusiastic about his job, and incredibly well versed in the history of Evan Williams. He made this tour a great experience and it seemed that every other person was just as happy as he was.

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Continuing on the Louisville Urban Bourbon Trail

If you’re not ready to call it quits, or if you’re looking for some alternatives to the stops above, here are some more of our favorite stops on the Urban Bourbon Trail.

Stop #7: Porch Kitchen & Bar

Attention Plant Eaters: You can find a delicious plant-based option here!

I couldn’t begin to tell you what my favorite thing was at Porch Kitchen & Bar. Our drinks were awesome. I drank a Rose & Fig which was Rosemary infused Jim Beam Black mixed with a fig simple syrup. Jason had their signature old fashioned which they made with black walnut bitters.

For dinner I had a Veggie Pattie Melt, which was a quinoa burger served with citrus aioli & havarti. YUM! If you’re looking for a great plant-based option in Louisville, this is it!

Detour: The Library at the Omni Hotel

If you enjoy a quiet place to grab a drink, this place is for you. The Library is yet another very cool hotel lobby bar that only opens in the evenings. Every detail in this place is perfect, from the big comfy chairs to the books that line the shelves. The menus are even printed on catalogue cards.

The best part about this place? You could actually hear the people sitting next to you! I have difficulty hearing when there’s background noise. I loved this place because there was no ambient music, just the sound of others talking. There seemed to be a lot of locals gathered here, which was surprising considering it was in the lobby of a hotel. There were large groups exchanging gifts, groups of young professionals meeting up after work, and a few tourists like us sprinkled throughout.

Stop #8: The Seelbach

While most places we’ve visited previously were great places to learn about history, no place shows you the history of this city quite like the Seelbach. It was a common place for Al Capone to visit and even had secret underground tunnels so these mobsters could evade police. The Seelbach is also featured in the F. Scott Fitzgerald book, The Great Gatsby. And, they even claim to have a ghost that roams their halls, who they’ve dubbed the Lady in Blue.

I can’t comment on the ghosts or the secret tunnels, but we did enjoy winding down at this quiet bar with a Kentucky Mule and a 1792 Small Batch before our second day (and final day of drinking) came to a close.

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End of the Trail

At this point you’ve collected all six stamps that you need to collect your prize. You can stop by the Visitor’s Center to claim your prize, or you can mail your passport to them at the address on the back page and they’ll send your prize to you.

With proper planning, responsible drinking, and plenty of snacks, Louisville is a fun drinking city. And thanks to Louisville’s Urban Bourbon Trail, there’s even a reward at the end. We didn’t know what to expect out of our trip to Louisville, but ended up having such a great time! If you love bourbon or if you’d like to learn more about it, you have to visit Louisville! There’s no other place in the world where you’ll get an expansive overview of the world of bourbon as you can in Louisville. Add this city to your short list of must-see destinations!

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