Being a huge bourbon enthusiast, the Bourbon Trail is my Mecca. This destination has been at the top of my bucket list since I became hooked on that magical brown liquor. There are officially 18 bourbon distilleries on The Bourbon Trail, 41 distilleries total spread out throughout the state of Kentucky, spanning from Louisville to Lexington to Bardstown. If you have ever been on a brewery tour, a bourbon distillery tour is very similar. It takes about 45 minutes to an hour and at the end is usually a tasting (~usually $5-$25 per person for a normal tour/tasting) . If you just want to skip straight to the tasting (I don’t blame you, some start to get repetitive), some distilleries allow you to do that. Some cost more than others and some takes weeks if not months in advance to schedule. The beauty of the trail is that it’s completely up to you on how you explore it. You can drive yourself or you can book a tour that drives you around (Highly recommend and the more people you can get the cheaper it is).
You don’t have to like bourbon to enjoy this trip. And the Bourbon Trail doesn’t have to be the main attraction. It wasn’t for us. We had a couple of guys on the bachelor party that weren’t bourbon fans and they still enjoyed themselves. You could make a long weekend trip of just exploring Louisville. Kentucky is a gorgeous destination, and overlooked in my opinion. You could center your trip around Louisville and spend one day on the Bourbon Trail like we did or you could spend 5 days on the Trail.
When I was originally planning to make this a solo trek, I was going to drive up from New Orleans, stopping at distilleries between Nashville and Louisville. But for the bachelor party we used Mint Julep Tours to drive us around. You can join a tour or you can create your own self-guided tour yourself. There is no wrong way to explore the Bourbon Trail.
I had high hopes for the Trail and it did not disappoint. But I was really surprised of how much I enjoyed Louisville (a.k.a. Bourbon City and Derby City). It’s one of those cities that has its own vibe, full of so much character. As soon as you step into the city you can feel it, from the old brick facades to the random Louisville Slugger statues and old clocks on the streets to the giant golden David statue to the random murals and distilleries scattered throughout the city. Typically I only visit cities once because I have too many places on my bucket list to visit. But there are a handful of places I make an exception for and visit again and Louisville is one of them.
Bourbon Trail / Louisville Itinerary:
Day 1 – Louisville:
Agave & Rye. I couldn’t have picked a better place for the first meal of the trip. Famous for their “Epic” tacos – crispy chicken tacos, Detroit pizza pie tacos, and lobster tacos – they also serve a fantastic birria. While you wait for your food you can play old arcade games for free. Next up were beers at Gravely Brewing. Why are you going to a brewery when you’re in bourbon country?? Because this trip was a marathon, not a sprint lol. Not only do they brew a great hefeweizen, but behind the bar are countless speakers, unlike anything I have seen at any other brewery. And up a flight of stairs is an outdoor patio with a great view of the city. While everyone was napping after playing drinking games, a few of us rented scooters to cross the Big Four Bridge into Indiana. Except our scooters stopped working half way on the bridge :/ (Didn’t know there are limits to where you can ride). After crossing into Indiana and walking the scooters back, we rode along the riverfront, taking pictures of Louisville Slugger Field and randomly stumbling upon the Lincoln Memorial Sculpture and the Big Four Bridge Viewpoint.
Day 2 – Bourbon Trail:
BOURBON TRAIL DAY!!!!!!! Nothing like being late to your own tour and pissing off the tour guide. Definitely don’t recommend. But Mint Julep Tours was awesome and waited for us and thank God they did. Sorry Tom! While driving yourself to the distilleries has its own benefit, being on a tour and having someone drive you is the way to go. They plan your day from start (8am) to finish (5pm), give you fun facts and a lesson on bourbon history while you’re driving, and take you to lunch.
1st stop: Lux Row. Not my favorite of the tour, but I enjoyed pairing bourbons with different chocolates.
2nd Stop: Bardstown. My favorite stop of the trip and the most unique. They let you sample bourbon STRAIGHT FROM THE BARREL!
3rd stop: Four Roses. This wasn’t on the agenda but since we were running ahead of schedule we stopped for a few mins at their gift shop.
4th stop: Stitzel-Weller. Founded by the bourbon master himself, Pappy Van Winkle. This was my second favorite distillery of the tour. The sights were beautiful and Kelsey was by far the best tour guide of the trip. And I learned about Blade and Bow’s 5 Key Club!
We all had dinner at Bar Vetti. What I am about to say is not hyperbole. BEST ITALIAN MEAL OF MY LIFE. Everything was amazing….the Focaccia, Ham & melon appetizer, meatballs, Bucatini, and tiramisu gelato. If there is one must meal of the trip, it’s dinner at Bar Vetti. Our waitress recommended to go to High Horse after dinner. Maybe it’s more livelier and has better live music on other nights, but we weren’t feeling their vibe that night. Instead, we should have went to Taj or Garage Bar, which seemed like more of our crowd. Not wanting to go out on that vibe, we luckily stumbled upon NuLu MarketPlace, a unique business hub whose tenants include West Sixth Brewing and other bars and shops, all surrounding a courtyard where you can hang out and drink.
Day 3 – More Louisville:
Day 3 was my favorite day of the trip. Had brunch and a much needed bloody Mary at the quirky Proof on Main. You can’t miss it, sitting behind the giant golden statue of David on Main Street. The restaurant’s restrooms are actually located in the Moremen Gallery next store so you get a free peak at some contemporary art on the way to the John. Guys, you’re gonna want to go #1 here. You’ll know when you see it…
My first horse race and it was at the Mecca of horse racing….Churchill Downs!!!! We all scootered 4 miles here from Main Street. It was a fun ride, getting to ride through some nice neighborhoods full of historic homes, reminiscent of Uptown New Orleans. Not without some bumps and bruises lmao Typically August is an off month at the Churchill Downs but the day we were there was Arlington Million Day, the only race day of the month. It’s a one day contest that hosts eleven thoroughbred races. You can stay for a few races like we did or stay for all eleven. If you want to place bets, you can do so from the comfort of your seat by downloading the Churchill Downs app. Seeing my horse win at the last second was such an adrenaline rush. Even if I only bet $5. Pay a little extra and sit in the shade and don’t forget to order a Mint Julep!!! It’s the official drink of the Kentucky Derby.
Needing a break from all the bourbon, we took a tour of Copper & Kings, a distillery for brandy, gin, and one of my favorites, absinthe. Needing a break from liquor, we walked a couple streets over to Ten20 Craft Brewery for some beer and pizza. Their Flying Pig paired well with a slice of pie. Last activity of the day was the Louisville City FC soccer game. FC plays in the second tier of the American soccer pyramid. Think of it as a minor league team for the MLS. It’s a cozy little stadium with a great atmosphere. Even if you’re not a soccer fan I think you could still appreciate it and have fun.
Day 4 – Louisville / Headed Back Home:
We tried to make the most of the morning before heading to the airport. Biscuit Belly was the perfect last meal of the trip. They don’t cook normal biscuits – S’mores biscuits, brisket biscuits, Nashville hot chicken biscuits, and the one I ordered, The Love Shack, with brie, honey, berry jam, and pralines on a biscuit.
After breakfast we hopped on the scooters one last time and drove past the Louisville Slugger Museum (home to the world’s largest baseball bat – 120 feet tall!!!) and Thomas Edison’s old house on E. Washington St., which is only a few blocks away from the Western Union where he worked in his younger days.
Where to Stay in Louisville:
We booked a place Downtown along the Ohio River through VRBO. Not only did we have great views of the river, but we were in close proximity to Museum Row (Louisville Slugger Museum & Factory, Muhammad Ali Center) and Whiskey Row. In fact, you don’t have to go very far on the Bourbon Trail to tour distilleries. You can walk to Rabbit Hole, Angel’s Envy, Michter’s and Old Forester from Downtown.
If hotels are more of your speed, I booked a room in the Omni Hotel for my originally planned trip. It’s located in Downtown only two blocks away from Old Forester and is affordable ($150-200 per night). Another hotel that caught my eye while doing research was The Grady Hotel. As a bourbon and bar lover, it has a stunning hotel bar and the building is full of history, once serving as a medicinal bourbon apothecary in the late 1800’s.
Walking back from the bars on Day 2, a neighborhood east of Downtown caught my eye called NuLu (“New Louisville”). It’s a trendy, up and coming neighborhood that looks like it belongs in New York City. It’s full of art galleries, boutique shops, bars, breweries, and restaurants and when I come back here, it is an area I want to stay in and explore more of. In fact, this is the area we scootered through on our last morning and ate at Biscuit Belly.
Transportation in Louisville and the Bourbon Trail:
Originally I was going to fly with budget airline Breeze Airways as they were the only airline that offered a direct flight from Nola to Louisville. But then they inexplicably stopped offering flights a couple weeks before the week of the trip and have now resumed its flights from Nola to Louisville. So I had to fly with Southwest and had layovers on both the departing and return flights.
As far as how to get around Louisville, you can get by without renting a car. I would only rent one if you’re going on the Bourbon Trail and not paying for a tour to drive you around. You can walk, bike, SCOOTER, Uber, and take the LouLift, a free electric bus that runs along Market & Main Streets downtown. If you’ve read my other travel guides, you know that scootering has become my FAVORITE means of transportation. Other than taking the tour bus to the distilleries, we scootered EVERYWHERE. There are scooters on just about every corner in Louisville. Just download the app of the particular scooter you want to ride, add your credit card to the app to pay for it, get on the scooter and go. It’s that easy. When you get to your destination, just park the scooter outside. The app will ask you to take a picture of the parked scooter as confirmation and click end ride. That’s it. Super convenient and so much fun to ride.
Another option I looked into when I couldn’t find a direct flight to Louisville was flying into Indianapolis (2 hours away) or Cincinnati (1.5 hours away). Obviously if you do this you’ll have to rent a car.
Bourbon Trail / Louisville Maps
Churchill Downs Tips:
- Depending on where you sit, there are certain dress codes for particular areas in Churchill Downs. Check out this link to make sure you don’t get turned away.
- You’re allowed to bring two water bottles and food into the racetrack.
- If you’re betting at a kiosk, only cash is allowed.
- Bring cash with you. While there are ATMs at the track, you don’t to be waiting in those long lines, potentially missing the races.
- Place your bets from the comfort of your seat using the Churchill Downs Racetrack app. You can also use this app to get your electronic tickets scanned at the gate.
- Minimum bet is $2.
- I’m the last person to take betting advice from, which is why you’re better off clicking this link to learn the basics of horse betting. If you want the cliff notes, know how much you want to wager, what type of bet you want to place (win = your horse has to win the race for you to win money; place = you win if your horse finishes first or second; show = you win if your hose finishes first, second, or third), and the number of the horse you want to bet on.
Bourbon Trail Tips:
- Book tastings weeks in advance, at least 4-6 weeks for most distilleries. When I was planning my original trip, Buffalo Trace did not have any available tastings 2 months out (Shocker because they’re one of the few distilleries that offer free tours and tastings).
- A lot of distilleries are either closed or have limited hours on Sundays, Mondays, and Tuesdays.
- KYBourbonTrail.com is a great resource for planning your trip, from using their itineraries to booking a tasting directly on their site.
- There are two ideal times of the year to visit in my opinion, late summer, when it’s warm during the day and cool at night, the sun doesn’t go down until almost 9pm, and you don’t have to deal with the Derby crowds; and during the winter when prices are lower, you’re inside the distilleries so you are out of the cold, and after all, bourbon was meant to drink when it’s cold!
Bucket List for Visiting Again:
- Louisville Slugger Museum ($18 per adult)– You can pretend to be an MLB star in the batting cages and you get to leave with your very own mini Louisville slugger bat!
- Visit the resting places of Muhammad Ali, Colonel Sanders, and Meriwether Lew Clark Jr. (The founder of Churchill Downs and the grandson of William Clark, half of the Lewis & Clark exploring duo) at Cave Hill Cemetery.
- Take a self-guided Civil Rights Tour, exploring the history of civil rights in Louisville, starting in the Civil War era. You can start the tour at the Muhammad Ali Center, where you can also explore the famous boxer and activist’s life. You can follow the tour using this online map, or you can pick up a printed copy as well as a Cave Hill Cemetery map at the Ali Center as well.
- Take a stroll in Central Park creator Frederick Law Olmsted’s other famous creation, Cherokee Park.
- Attend the free Kentucky Shakespeare Festival at Louisville’s Central Park from late May to early August. Who knew Louisville had a theatre scene??
- Try a Hot Brown from Buck’s in Old Louisville, Louisville’s most famous dish.
- Attend a tasting at Louisville’s downtown distilleries: Angel’s Envy (Aged in port wine barrels; they make my favorite rye), Michter’s (Currently my favorite bourbon, so smooth it’s almost creamy), and Rabbit Hole (The founder quit his psychiatry practice of 20 years and took the plunge down the Rabbit Hole to distill bourbon instead).
- Try a one-ounce pour at Neat (Located in Bardstown) 200 vintage bourbons, ranging from $5 to $200!
- Dip your own bottle at Maker’s Mark.
- Have a drink at Hell or High Water (Reservations are required), a hidden speakeasy located on the backside of Whiskey Row. To find it, you first have to find Hello Curio, an art gallery that marks the entrance to the speakeasy. Once you arrive at the gallery, a host will show you to the speakeasy.
- Take a day trip to Mammoth Cave, where you can take a self-guided tour ($8 for adults) of the world’s longest cave system.
- Spend more time in Bardstown, “The Bourbon Capital of the World“!!
- Attend the Kentucky Derby Festival – Louisville is lit with fireworks, steamboat races, and parades for the two weeks preceding Derby Day.
- Instead of blowing hundreds if not thousands of dollars on Kentucky Derby tickets, join the locals on Thurby (Thursday before the Derby) or the Oaks (Friday before the Derby). Races on these days are much cheaper and usually less crowded.
