Beyond Bourbon: Our Road Trip Guide From Lexington To Louisville, Kentucky

The Uproxx Fall Travel Hot List is finally here! And with it, some serious love for Kentucky, long known as the bourbon capital. That title is well-earned, the state draws over 2.5 million visitors per year from all over the world to its famed Bourbon Trail. With 73 (and counting) distilleries in the state, it is an obvious destination for whiskey enthusiasts. So when I told my friends I was going on a road trip through parts of northern Kentucky they all had basically the same — very excited — response: “FOR A BOURBON TOUR?”

“No,” I replied over and over, watching their faces visibly fall, “my plan is actually to hike and drink wine and find some hidden gems — preferably down a dirt road that has inspired at least one country song.”

When my friends looked at me incredulously, I was sure to add, “Okay, fine — maybe I’ll drink a little bourbon along the way.”

“Oh you’re probably visiting a new national park then?” a few tuned in friends added.

But I wasn’t doing that either. I’ve already visited — and was mesmerized by — Mammoth Cave National Park in Southern Kentucky. This time I simply wanted to see what else the state had to offer — beyond bourbon and the national park I knew it for.

So that’s just what I did. I flew into Lexington for some outdoor adventure, then road-tripped north to Louisville for some history. Here is my guide:

Day 1 — Lexington:

lexington Kentucky
Emily Hart

I started my road trip in Lexington, the horse capital of the world. It’s just about 75 miles from Louisville but had a decidedly more laid-back vibe. After picking up my rental car I was in awe of the wide open spaces and country roads that seemed to go on forever. As the second most populous city in the state, I quickly found that it has just the right combination of slower Southern charm along with adventurous activities.

I checked into the Home2Suites, which was perfectly located for the adventures I had planned. I loved having a clean and simple suite (that let’s be honest was still more spacious than my apartment back home in Boulder) to rest and relax after spending time exploring. It was perfectly clean, had great staff, a pool, and a cool lounge area outside, and despite being a chain hotel (with a terrrrrrrible name) was actually walkable to several bars, restaurants, and coffee shops. All while being near the I-75 interstate, cutting down on my driving time.

First Stop — Zip Lining at Boone Creek Outdoors

boone creek outfitters
Emily Hart

After check-in, I was quickly on to my first adventure, zip-lining. Now, intellectually, I know zip lining is perfectly safe and that thousands of people enjoy it every day. But if I’m being honest, I have been irrationally terrified of doing it for years. I have often found myself in beautiful destinations staring up at zip lines and every time I politely decline any offers. “Just not for me,” I say as calmly as I can while inside I’m screaming, “HELLLLLLL NO.”

So I hyped myself up on the drive over, reminding myself that I didn’t have to do anything I didn’t want to do, but that I also wanted to do this. I wanted to try.

“Have you ever been zip lining?” the friendly front desk attendant at Boone Creek Outdoors asked me with a comforting Kentucky drawl.

“I haven’t,” I replied.

“Are you afraid of heights?” he pressed.

My face gave me away. “I am.”

“Well, we’ll work on both of those today.”

zip line kentucky
Emily Hart

Boy, did we. We started small and worked our way up to a nearly 1,400-foot-long zip line over the 200-foot-deep gorge. It was heart-pumping like I had imagined, but also the most fun I had had in months. Maybe longer.

Flying through the gorgeous tree canopy, taking in the incredible gorge that surrounded me, and the southern hospitality of my guides put me at ease in a way that felt like an actual life breakthrough. I felt capable and strong and ready to see more of this absolutely beautiful land that I had just flown through.

Second Stop — Talon Winery

Talon Winery
Emily Hart

I wanted to keep riding on the high from my successful zip-lining experience, so I looked up wineries nearby and beelined over to Talon Winery. Tucked away on 300 acres of pristine Kentucky farmland, the property is absolutely dreamy. I spent some time as the only patron in the winery for a tasting, enjoying the Kentucky hospitality (you’ll hear a lot about this) and, of course, the wine itself.

Talon Winery
Emily Hart

I happily bought a bottle of Moondance, a Pinot Gris with a citrus nose, to enjoy outside (and re-cork for later in the trip) and nearly cried because it was such an idyllic scene. Groups of hip younger patrons came and went (and selfied among the vines) as I sat with my book and the Kentucky sunset that just hit differently.

Third Stop — Drake’s Come Play

drakes come play lexington
Emily Hart

After I got back to my hotel I was hungry but way too tired to drive anywhere else (I also wanted to be able to uncork my bottle of Talon wine safely) so I walked the very short distance from my hotel to Drake’s Come Play. A Lexington-based regional chain restaurant, Drake’s Come Play has a wide variety of menu items (including burgers, tacos, steaks, and sushi) and a laid-back sports bar vibe.

I enjoyed the fried fish entree with a glass of rosé before heading back to my room to rest up for the big day that was ahead of me.

Day 2 — Kentucky State Parks

There are 45 state parks in Kentucky, and I knew I wanted to visit some while I was in the state. As an avid hiker and National Park traveler who spends a lot of time west of the Mississippi, Kentucky feels like a hidden gem. There are almost endless outdoor recreation opportunities in the Bluegrass State, but as my time was limited I opted for an area where two parks — Red River Gorge National Geological Area and Natural Bridges State Park — meet.

First Stop — Red River Gorge National Geological Area and Natural Bridges State Park

KY State Park
Emily Hart

Just about an hour’s drive from Lexington lies the Red River Gorge National Geological area. I was excited to wake up early on my second day in Kentucky and experience this area of the Daniel Boone National Forest as it came highly recommended by the zip-lining guides. I could see why immediately.

Red River Gorge is known for rock climbing, consistently lauded as the sport climbing capital of the country, but I was most excited to see some of the 150 sandstone arches in the area, the only area east of the Rocky Mountains with as many. I went on a few short hikes and was blown away by each one.

I recommend Cloudsplitter and Gray’s Arch Trail.

KY State Park
Emily Hart

Adjacent to Red River Gorge is another stunning natural wonder, Natural Bridges State Resort Park. This park has a lot to offer from hiking to natural arches, camping, a restaurant, a gondola, a history center, and lodging. You could spend much longer than a day here. During my trip, I spent time hiking the Natural Bridge and Low Gap Trails and was impressed at each turn by the landscape and tranquility.

Second Stop — Miguel’s Pizza

You can’t visit the Red River Gorge area without a stop at Miguel’s Pizza. It may look like Miguel’s Pizza is just your average roadside pizza parlor, but it’s legendary in the Red River Gorge. For the past 30 years, Miguel Ventura and his family have worked to build not just tasty pizzas, but a mecca for climbers from all over the world. You see, Miguels is also a gear shop and campground for visiting climbers, who can sometimes number in the hundreds during a busy night.

Miguel's Pizza
Emily Hart

As I enjoyed a few slices of pie and a local brew, I marveled at the almost utopian feel of the grounds. The mix of tourists passing by and climbers who were resting and comparing notes made this a truly memorable roadside meal.

Day 3 — Louisville

First Stop — Kentucky Derby Museum

KY Derby Museum
Emily Hart

On my third morning in Kentucky, I checked out of my hotel in Lexington and started the short drive to Louisville. As the most populous city in the state, it’s known for bourbon and, of course, the Kentucky Derby. I admittedly don’t know much about horse racing, so I decided to drop by Churchill Downs to tour the Kentucky Derby Museum. You can take several tours from the museum, and I opted for the historic walking tour. Our guide took us out through the grandstands to the rail of the track, giving us stories and insight into what The Derby was and how it transformed into what it is today.

Then came the best part, mint juleps. I stopped by the Derby Cafe and Bourbon Bar to indulge in a famed Kentucky Derby staple before heading downtown.

Second Stop — Historic Walking Tour

Louisville Walking Tour
Emily Hart

I travel for a living and have experienced many guided activities throughout the country. But one thing I’d never experienced is also one of the simplest, a walking tour. I like the freedom of exploring and walking around on my own. But in a town as historic as Louisville, I wanted to get some more context and I’m so glad I did.

I booked a walking tour of Louisville’s Historic District with Louisville Historic Tours. I joined a few other visitors on a street corner on the border of “Old Louisville” to meet our guide, the impressive author David Domine. As he walked us around the neighborhood, he explained not just the history of the area, but of the architecture, the famous residents, and even urban legends in the area.

It was a beautiful way to spend an afternoon and get a little off the beaten path.

Third Stop — Check in at Moxy Hotel in Downtown Louisville

Moxy Louisville
Emily Hart

Right as I got back to my car after the walking tour it started to rain, so I was happy to go check in to my hotel downtown and relax a bit. Located right off of Louisville’s famed Main Street (Whiskey Row), the Moxy Hotel is unique and fun. Check-in is at the bar — with a welcome drink of course — and then a chalkboard-painted elevator took me to my stylish corner room.

The Moxy Hotel brand has locations all over the world and is owned by Marriott, but the experience feels high-end boutique. The hotel’s bar and restaurant — Zombie Taco — is dark and vibey with fun drinks and tasty tacos. I loved the floor-to-ceiling windows throughout my room and the playful touches throughout.

Fourth Stop — Explore Downtown Louisville

Downtown Louisville
Emily Hart

After the rain let up a bit I was excited to explore downtown Louisville. Luckily, I was situated perfectly at the Moxy to walk to all of the bars and museums I wanted to visit on Whiskey Row.

21C Museum Hotel Louisville
Emily Hart

My first stop was the 21c Museum Hotel Museum and Bar, a tip from my tour guide David. While I had read about 21c Museum Hotels many times, this was my first visit and I was blown away. Based in Louisville, 21c Museum Hotels are now in several locations throughout the Midwest and South. The combination of art, museum, and boutique hotel feels fresh and inventive and I was happy to explore the grounds.

The exhibits in the 9,000-square-foot museum were contemporary and thought-provoking, and the drinks at the hotel bar and restaurant, Proof on Main (one of our favorite spots), were interesting and felt bespoke. I can’t wait to return and stay on the property longer.

Louisville Slugger Museum
Emily Hart

After spending time at the museum and bar, I spent hours strolling along Main Street and popping into several places. I wish I had time for everything. But on a shorter trip, I wouldn’t miss the Frazier Kentucky History Museum, Louisville Slugger Museum and Factory, and the Michter’s Fort Nelson Distillery and Bar.

Doc Crows
Emily Hart

For dinner, I popped into Doc Crow’s Southern Smokehouse and Raw Bar where I enjoyed another mint julep and a catfish platter with hushpuppies and pickled vegetables, the most “Southern” meal I can think of which was also the most delicious of the trip.

Day 4

Emily Hart

First Stop — Run Across the Big Four Bridge

big four bridge
Emily Hart

I woke up bright and early on my last day in Kentucky to explore the riverfront, specifically the Big Four Bridge. What was once a railroad truss towering over the Ohio River, has been repurposed into a pedestrian walkway. I ran across through walkers and bikers of all ages enjoying the view and crisp morning air. The entire waterfront area is frankly impressive for a city this size. The 85-acre natural area feels like a respite but is just steps away from the hustle of Whiskey Row.

Next time, I’d love to come back for sunrise or sunset.

Second Stop — Copper & Kings Distillery Tour

Cooper and Kings
Emily Hart

While I didn’t come to Kentucky for distillery tours, I would be remiss to leave the state without going on one, right? Whatever the justification, you can’t really go wrong with any of the distilleries in Louisville.

Many of the big-name distillery tours require reservations and tickets that book up well in advance, so I looked outside the staples and found Copper & Kings Distillery, which makes American brandy instead of the ubiquitous bourbon and rye whiskey you find at all the other distilleries. First, I joined a few others on a distillery tour, learning about the traditional copper pot distillation that they use, and their method of “sonic aging” where Copper & Kings plays music from several subwoofers toward their barrels in the basement maturation cellar 24/7.

Copper and Kings
Emily Hart

After the tour, we were able to taste several of the gins, brandy, and even absinthes that Copper & Kings produce before I headed up to the rooftop restaurant for a quick bite and a drink before heading back to the airport. It may have been against my brand to not focus on National Parks and against KY’s brand to have a tourist only visit one distillery but it was the exact trip I needed and one I’ll be recommending often!