How To Take The Ultimate Vacation In Louisville, Kentucky

Fans of history, bourbon, live music and baked goods will find plenty to do in River City.
Illustration: Damon Dahlen/HuffPost; Photos: Getty

Take A Break is your ultimate guide to the perfect trips to recharge, rediscover yourself and your relationships, and reengage with the world. We’ll cover shopping stops, great bars, restaurants worth your money, photo opportunities, memorable drives and experiences, and other important details you need before you book.

Below, we chat with Caroline Bologna, senior travel and culture reporter at HuffPost, about why you’ll want to put Louisville, Kentucky, on your bucket list.

What drew you to Louisville as a place to visit or explore?

My mom grew up in Kentucky, so a lot of my extended family is in Louisville. When I was younger, we used to drive up there from my hometown of New Orleans for holidays, and in recent years, I’ve made a number of trips for weddings and other occasions.

What are the best times of year to visit?

I’ve been to Louisville in every season, but my favorite is probably spring. If you aren’t planning to attend the Kentucky Derby, don’t book your trip for that weekend, as prices will be astronomical. But I recommend going in the weeks and months leading up to Derby Day because there’s a lot of excitement and the weather tends to be nice and mild.

What’s your best tip for getting there? How can you make the travel as stress-free as possible?

Louisville Muhammad Ali International Airport is accessible from most major United States hubs, so it’s not too hard to find flights that are nonstop or only require one connection. If you’re looking for even more options, Cincinnati/Northern Kentucky International Airport is larger and located only about 90 minutes from downtown Louisville.

From left to right: 21c Museum Hotel, Louisville Muhammad Ali International Airport, and a backyard mint julep.
Caroline Bologna/HuffPost
From left to right: 21c Museum Hotel, Louisville Muhammad Ali International Airport, and a backyard mint julep.

Where do you recommend staying when you go?

I’m a fan of the 21c Museum Hotels chain, which is actually based in Louisville. These boutique hotels contain impressive contemporary art galleries for a unique guest experience. The original location is right in the heart of downtown Louisville in a grouping of renovated 19th-century warehouses and also has a great restaurant called Proof on Main.

For something more historic, The Brown Hotel was built in 1923 and is famously the birthplace of the “Hot Brown” open-faced sandwich, a local delicacy. This hotel is also located in downtown Louisville, but adjacent neighborhoods like Old Louisville and NuLu (New Louisville) also have nice hotels and rentals.

What are your go-to restaurants or foods to eat while you’re there?

I have a major sweet tooth, so I can’t get enough of Plehn’s Bakery, a family-owned spot that dates back to the 1920s. The iced sugar cookies and angel dips are my favorites, but honestly everything is delicious. Hi-Five Doughnuts is also solid.

When you’re in Louisville, try a slice of Derby pie if you see it on the menu anywhere. And if you buy a coffee at Please & Thank You, be sure to get one of their chocolate chip cookies as well. For frozen treats, I enjoy The Comfy Cow, Louisville Cream, Graeter’s and Homemade Ice Cream & Pie Kitchen.

As for savory eats, Wagner’s Pharmacy is an iconic diner that opened in 1922. Jack Fry’s is another Louisville landmark going back to the ’30s. I’ve heard great things about Ramsi’s Cafe on the World and the barbecue offerings at Feast and Momma’s Mustard, Pickles & BBQ as well.

When I’ve visited family in Louisville, they’ve taken me to Mesh. For breakfast, I’m a huge fan of Biscuit Belly and Wild Eggs, which both have multiple locations. Blue Dog Bakery is also great (and you can try their bread at Mesh as well).

From left to right: Dessert at Mesh, breakfast at Biscuit Belly and treats from Plehn's Bakery.
Caroline Bologna/HuffPost
From left to right: Dessert at Mesh, breakfast at Biscuit Belly and treats from Plehn's Bakery.

What bars or entertainment spots do you make sure to hit? What’s good to drink there or what else should people know?

A popular move for those visiting Louisville is to schedule a bourbon-related tour. You can visit distilleries within the city or venture beyond its bounds to follow the full Kentucky Bourbon Trail. Even if you don’t go for a full-on bourbon experience, make sure to try a mint julep while you’re in town.

As for specific bars, there’s Hell or High Water and 8UP Elevated Drinkery & Kitchen in the downtown area. Fourth Street Live! is a big entertainment and dining complex nearby where you can grab a drink and listen to live music.

What are your favorite shops and what do you look for when you’re there?

I love shopping for stoneware in Kentucky. Hadley Pottery was always my favorite, so I was devastated to learn it’s going out of business later this year. If you find yourself in Louisville before the shop fully closes, try to buy a piece or two. Otherwise, Louisville Stoneware is another favorite and seems to be going strong.

Scout and Monkee’s are cute boutiques located near Mesh that I like to stop by when I’m in the Crescent Hill area. I also enjoy browsing Butchertown Market.

What’s your single favorite spot to go for photos and why?

The Louisville Slugger Museum & Factory is a really fun place to take pictures since it has a giant bat out front. Perfect photo op!

It’s also not too far from the golden replica of Michelangelo’s David statue, which is almost double the size of the original in Italy.

What tourist attraction should people skip and what should they do instead?

Touring the Kentucky Derby Museum at Churchill Downs can be cool, but if horse racing isn’t really your thing, consider visiting the Speed Art Museum or Muhammad Ali Center instead. You can also see Ali’s gravesite (as well as the grave of KFC founder Colonel Harland Sanders) at Cave Hill Cemetery.

From left to right: Louisville Stoneware, the Louisville Slugger Museum & Factory, and Homemade Ice Cream & Pie Kitchen.
Caroline Bologna/HuffPost
From left to right: Louisville Stoneware, the Louisville Slugger Museum & Factory, and Homemade Ice Cream & Pie Kitchen.

Where do you feel the most relaxed, calm or happy?

Strolling around the waterfront area is very pleasant. You can even walk or bike from Louisville to Indiana via the Big Four Bridge. There’s also the Belle of Louisville if you’re into riverboat cruises.

What scenic spots do you recommend checking out?

Old Louisville boasts the largest contiguous collection of Victorian mansions in the U.S and the largest collection of pedestrian-only streets in any neighborhood in the U.S. There are lots of charming walking paths and you can take organized or self-guided tours.

If you don’t mind driving about 75 miles outside the city, take advantage of the opportunity to visit the famous Mammoth Cave National Park as well.

What’s one thing you make sure to pack if you’re going and why?

I try to leave space in my suitcase and pack mostly soft items so I can bring back pottery or a couple of new Derby glasses.

What are some specific planning tips to know before you go so you’re not stressed?

While there are walkable areas in Louisville and plenty of Ubers, I recommend renting a car if you’re planning to cover a lot of ground. But note: If you do rent a car, prepare for a lot of inconvenient one-way streets.

What surprised you about Louisville when you went the first time?

I was a baby when I first went, so most things would have been a surprise to me! Returning as an adult, I’ve been struck by the way Louisville is sort of a blend of the South and the Midwest. The city doesn’t feel particularly Southern or particularly Midwestern, but it contains elements of both cultures and thus offers its own unique vibe.

Anything else visitors should know?

Resist the urge to pronounce it “Louie-ville.” Locals tend to go with “Loo-a-vuhl.”

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