How to Take the Ultimate Vacation in Louisville, Kentucky

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

Below, we talk to Caroline Bologna, Senior Travel and Culture Reporter at HuffPost, about why you’ll want to put Louisville, Ky., on your to-do 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 there from my hometown of New Orleans for vacations, and in recent years I’ve made a number of trips for weddings and d other occasions.

What are the best times of year to visit?

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

What’s your best advice for getting there? How to make the trip as stress-free as possible?

Louisville Muhammad Ali International Airport is accessible from most US hubs, so it’s not too difficult to find non-stop or one-connection flights. If you’re looking for even more options, Cincinnati/Northern Kentucky International Airport is larger and located only about 90 minutes from downtown Louisville.

Caroline Bologna/HuffPost

Left to right: The 21c Museum Hotel, Muhammad Ali International Airport in Louisville, 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 group of renovated 19th century warehouses and also features an excellent restaurant called Proof on Main.

For something more historic, The Brown Hotel was built in 1923 and is famous for being the birthplace of the local specialty “Hot Brown” open sandwich. 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 favorite restaurants or foods during your stay?

I have a big sweet tooth, so I can’t get enough of Plehn’s Bakery, a family-run place that dates back to the 1920s. The glazed sugar cookies and angel dips are my favorites, but honestly everything is delicious. Hi-Five Donuts 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 from Please & Thank You, be sure to get one of their chocolate chip cookies too. For frozen treats, I like The Comfy Cow, Louisville Cream, Graeter’s, and Homemade Ice Cream & Pie Kitchen.

As for savory dishes, Wagner’s Pharmacy is an iconic restaurant that opened in 1922. Jack Fry’s is another Louisville landmark that dates back to the 1930s. I’ve heard good things about Ramsi’s Cafe on the World and barbecue offerings from Feast and Momma’s Mustard, Pickles & BBQ.

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

From left to right: Dessert at Mesh, breakfast at Biscuit Belly and sweets at Plehn's Bakery.

Caroline Bologna/HuffPost

From left to right: Dessert at Mesh, breakfast at Biscuit Belly and sweets at Plehn’s Bakery.

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

A popular decision for those visiting Louisville is to plan a bourbon-related tour. You can visit distilleries in the city or venture beyond its limits to follow the entirety of the Kentucky Bourbon Trail. Even if you’re not going for the full bourbon experience, be 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 city center. Fourth Street Live! is a large entertainment and dining complex nearby where you can have a drink and listen to live music.

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

I love shopping for sandstone in Kentucky. Hadley Pottery has always been my favorite so I was devastated to hear it was closing later this year. If you find yourself in Louisville before the store is completely closed, try to buy a piece or two. Otherwise, Louisville Stoneware is another favorite and seems to be going strong.

Scout and Monkee’s are nice shops near Mesh that I like to stop by when I’m in the Crescent Hill area. I also like to browse the Butchertown market.

Where is your favorite place to take photos and why?

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

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

Which tourist attraction should people avoid and what should they do instead?

Visiting the Kentucky Derby Museum at Churchill Downs might be cool, but if horse racing isn’t really your thing, consider visiting the Speed ​​Art Museum or the Muhammad Ali Center instead. You can also see Ali’s grave (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 most relaxed, calm or happy?

Strolling on the seafront is very pleasant. You can even walk or bike from Louisville to Indiana via the Big Four Bridge. There is also the Belle of Louisville if you like riverboat cruises.

What scenic spots do you recommend visiting?

Old Louisville has the largest contiguous collection of Victorian mansions in the United States and the largest collection of walkable streets of any neighborhood in the United States. There are many lovely hiking trails and you can take organized or self-guided tours.

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

What is the thing that you make sure to take with you if you go and why?

I try to leave room in my suitcase and pack mostly soft items so I can bring home some pottery or a few new Derby glasses.

What specific planning tips do you need to know before you go so you don’t get stressed out?

Although there are pedestrian areas in Louisville and plenty of Ubers, I recommend renting a car if you plan to cover a lot of ground. But beware: if you rent a car, be prepared for many inconvenient one-way streets.

What surprised you in Louisville when you first went there?

I was a baby when I first went so most things would have been a surprise to me! Back as an adult, I was struck by how Louisville is kind of a mix 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 choose “Loo-a-vuhl”.

About Margaret L. Portillo

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