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The Perfect Weekend Getaway: Louisville and Bourbon Country From Chicago or Atlanta

Our new series on weekend road trips aims to inspire you for what's to come as we slowly return to travel.

Covid-19 Disclaimer: Make sure to check the status of the states, regions, and establishments in which you’re planning to visit prior to travel. Many regions continue to see high infection rates and deaths, while many states and counties remain under varying stay-at-home orders. Those traveling from areas with high rates of Covid-19 should consider avoiding travel for now in order to reduce spread.

A five-hour drive south of Chicago or a six-hour drive north of Atlanta lies Louisville, the Northern Kentucky city home to more than just the horse race it tends to be known for. Whether you’re looking for great eats, a bourbon experience you can’t get elsewhere, or a moment away from the hustle and bustle, this friendly city that brings Southern-hospitality a little further north has something for everyone.


Driving from Chicago to Louisville is a pretty straight shot south. From Chicago, you’ll hop on 1-65S and then drive for a little under five hours. Louisville will be your first exit when crossing into Kentucky. From Atlanta, zip across I-75N and I-24W through Nashville to I-65N.

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One of the great things about Louisville is that it’s a small city. This means that, even when downtown, parking is a non-issue. Coming from Chicago where street parking is a rarity and garage rates cost an arm and a leg, this is quite the relief for a family whose hotel check-in might not come until later in the afternoon. Rather than heading to your hotel to park, you can start the day off right by heading straight to breakfast in the cool, east-of-downtown neighborhood, Nulu.

Try out Biscuit Belly, a newer breakfast spot that has quickly become a hit for people living in the Kentuckiana area. It brings people from the city and those from across the bridge who are looking to start their morning right—with a biscuit! Because of its popularity, expect a short-wait that will be well worth it.

And for your caffeine fix, head towards Please & Thank You. While the coffee is delicious, the cookies, that even hours later goo like they were just pulled from the oven, are the real draw.

While this neighborhood might be most popular for their trendy restaurants, they also have a collection of local shops, giving you the chance to find unique pieces to bring home with you. Check out Red Tree Furniture, Scout, and Revelry Boutique Gallery. And if you find yourself in the city on the second weekend of the month, visiting the Flea Off Market is a must. This outdoor, monthly pop-up flea market brings together local vendors, artists, restaurants, coffee shops, and musicians.

Nicolas Henderson/flickr

For lunch, we’re staying in Nulu and heading to the restaurant Louisville loves: Royals Hot Chicken. This counter-service stop offers hot chicken (though the different levels of heat welcome those with a more sensitive palate), southern sides, and boozy slushies.

After lunch, we’re heading downtown to explore the city’s museums. If you’ve got a kid, not stopping at the Kentucky Science Center would be sinful as it’s incredibly interactive. Other great stops include the Frazier History Museum, Muhammad Ali Center, and Center for the Arts, which houses small and large scale plays and musicals.

To start the night off right (with a cocktail), simply look for the giant, golden, seemingly out of place reproduction of Michelangelo’s David. While the statue might be a sight for sore eyes, behind it lies the 21 C Hotel, which houses a restaurant and bar on their first floor. After grabbing a drink, you can head around back to their totally free (and very funky) art museum.

To avoid an added drive, we are keeping dinner downtown—but don’t worry, the food here is just as good as that in Louisville’s eclectic neighborhoods. You could try Sidebar, on Whiskey Row, for a gourmet burger, fries, and a chilled glass of the state’s famous beverage. Or if an Italian dinner sounds nice, Vincenzo’s. And if you’re really hoping to get a taste of the city, stop by The English Grill, inventor of the hot brown.

After dinner comes a night out. While it might be a little cheesy, doing a night at Fourth Street Live is a Louisville-must. At night, the area shuts down to those under 21 and bars open their doors and start pouring! Each city has their area that’s a little gimmicky, a little rowdy, but ultimately a fun night out—Fourth Street Live is Louisville’s.


We’re kicking day two off in Louisville’s Highland and Crescent Hill neighborhoods, the areas that are all about “Keeping Louisville Weird.” The two are an easy drive from one another, so breakfast in one and shopping in the other is totally feasible.

In the Highlands is Highland Morning, a brunch spot with an incredibly expansive menu. While the large menu might not be the most thrilling/inventive, the food is always good—nothing wrong with a simple breakfast done right! Eggs Over Frankfort, in Crescent Hills, is another great option. Eggs are in the title and boy do they do them right, but don’t overlook the biscuits and gravy or cinnamon rolls, which frequenters know are just as good as their titled dish.

Both of these areas are great for walking around and shopping local. Consider checking out Carmichael’s Bookstore, which has a location on both Bardstown Road and Frankfurt Avenue. This is Louisville’s oldest independent bookstore—the perfect place to find a read for the drive home! In Crescent Hill, you’ll also find Cherokee Park, which is the perfect place for a short or long walk, mild hike, or to take in the stunning houses that surround the green space.

For lunch, try Crescent Hill’s Irish Rover, an Irish restaurant with a large selection of brews and traditional Irish cuisine. Or if you’ve stuck to the Highlands, Bunz Burgers, or Taco Luchador. Both offer a cheap and easy meal, as well as solid vegetarian options.

Given that bourbon is the drink of Kentucky, leaving the city without getting a sip of its claim to fame would be a serious mistake. After lunch, spend your afternoon exploring Bourbon Trail (though the name might indicate walkability, these distilleries are scattered, so you’ll likely want to pick one section to explore).

Jeremy Thompson/flickr

Downtown distilleries include Old Forester Distilling Co., Kentucky Peerless Distilling Co., Jim Beam Urban Stillhouse, and more. And if you’re looking to venture outside of downtown, you can head towards the Brown Forman Distillery or Stitzel-Weller Distillery. There are endless options—this trail can take you as little or as long as your heart pleases and your liver can handle.

Last night we spent dinner downtown, so for night two we are going to branch out and explore what different neighborhoods have to offer. Though Louisville may not be famed for their BBQ in the way that Kansas City or Memphis is, it doesn’t mean that it’s not good. Feast BBQ, a counter-service restaurant in Nulu, has quickly become one of the city’s go-to spots for good Southern BBQ. They offer sandwiches, plates, racks of ribs, and every comforting side you can think of. For a less trendy (but still totally delicious) option, you can head back toward Crescent Hills for Frankfort Avenue Beer Depot, BBQ that has spent all day in the smoker. With tons of outdoor seating, a small putt-putt course to keep your kids (or you!) entertained while you wait, and pitchers of cheap beer, this dive is worth the short Uber ride.

After dinner, your options for the night vary wildly but hear me out because both are well worth your time—you can spend night two at Churchill Downs or at the city’s haunted sanatorium. Downs After Dark is an event that happens on Saturdays throughout the summer and has become a favorite among Louisville’s 21+ crowd. It’s a chance to see the track, place some bets, drink, and hear live music.

INSIDER TIPCheck the website before you go, as most nights tend to have a theme (and it’s suggested to dress accordingly).

And for an activity with no age requirement, you can visit Waverly Hills Sanatorium for a Ghost Tour. Even if you’re not a ghost believer, there’s something exciting (and a little spooky) about a ghost tour—and it’s something kids can join in on! This building is an old hospital once considered one of the most haunted places on earth (Ghost Hunters and Ghost Adventures have been here if that tells you anything). Hear stories of the sanatorium and look for their most infamous ghosts!


It’s the last day of your weekend getaway, and we’re starting the morning at the Big Four Walking Bridge. For a very long time, this bridge that spans the Ohio River was out of commission, so Kentucky and Indiana teamed up to fix-it-up. It now serves as a walking bridge, connecting the two states and dropping you off by some great parks and shops.

A walk across the bridge will put you in Jeffersonville, Indiana, a wonderful place to grab breakfast before heading back across. Consider stopping at Adrienne’s Bakery for a morning sweet, Early Edition or Geraldine’s Kitchen for a classic American breakfast, or Pearl Street Coffee House for those that need a little caffeine to start their day.

Downtown Jeffersonville offers lots of local shopping (conveniently right off the bridge). If you’re going to make a stop anywhere, it has to be at Schimpff’s Confectionery, which has been around since 1891. This spot makes their own Red-Hot candies that you can watch being created from inside or the window (but inside viewers get to sample).

Across the bridge back in Louisville, you can also rent bikes or enjoy the Waterfront Park, offering various playgrounds and areas to roam for kids needing a little time for structure-less play.

For lunch, we’re heading out of downtown. Cunningham’s Creekside is a seafood restaurant that has been around for ages (though this location is new), and their fried fish sandwich is something of Louisville lunch-time staple. And for a simple soup and sandwich, head over to the family-owned Cottage Café.

INSIDER TIPThe desserts are what you come for and are known to sell out, so, if you’re wanting a piece of pie or cake, consider ordering it first.

For the last afternoon in Louisville, we want to make sure we’re spending it right. For those wanting to get a look at the famous Churchill Downs in the daylight, a tour of the track and Kentucky Derby Museum is a must. And for those seeking a little thrill, head toward Kentucky Kingdom for a huge waterpark and exciting rollercoasters!

Insider Tip: This theme park was once owned by Six Flags, so, though the name has changed under new ownership, the rides have pretty much remained the same.

Our last stop has to be at Vietnam Kitchen which, despite a less-than-stunning exterior (ignore that it’s in a strip mall), has consistently voted one of the best eats in the city! Their menu is incredibly expansive, which can be overwhelming, but rest assured, there is no bad thing. Starting with the steamed shrimp roll and peanut sauce is the best way to kick-off your dinner here.


Wonder what it’s like to stay inside a kaleidoscope? The 21 C Hotel has the answer and room for you. Though it is expensive, it’s also remarkable! For a less artistic take on the hotel, the Galt House will be a safe bet (and the rotating restaurant at the top does add some funk).


The best time to visit is during the spring, summer, and fall. While Louisville might be considered part of the South, it does get quite frigid, and sometimes snowy, in the winter, making time spent outdoors a little more difficult. Also, it should be noted that the summers are hot and humid, but if you pack accordingly, totally manageable!