The Highlands is most well-known for three things: its oddity stores, its stretch of bars, and its diverse selection of restaurants. While most tourists to Louisville head down to Fourth Street Live for a night on the town, most locals head to the stretch of Bardstown Road that is home to the Highlands' bars, pubs, and clubs. The following drinking establishments can be found in Louisville's Highlands.
Akiko's is one of the signature hole-in-the-wall bars that are so popular in the Highlands. Karaoke is hugely popular at Akiko's, but good luck getting your name pulled out of the hat to sing. The one time I went drinking at Akiko's, we couldn't figure out how people knew it was their turn to sing, and we waited for over an hour to sing before finally leaving because our names were never called. Akiko's also only sells beer, cheap wine, and Saki, so it's not the place to go if you're out to drink cocktails.
Many people argue that the Bambi Bar has some of the best burgers in town. I've not ever personally eaten a burger there, but I've heard good things about them from enough people to believe the statement holds some truth. The bartenders are friendly and the establishment really has the feel of a neighborhood bar more than some of the trendier bars on Bardstown Road.
If you like hot wings, beer, and sports, then you'll like drinking at Buffalo Wild Wings. Buffalo Wild Wings is one of the more mainstream bars in the Highlands. The bar and restaurant is hopping on big game nights when there is typically some sort of wing special in addition to the game being played across the restaurant's many big screen TVs. When its not a game night, Buffalo Wild Wings isn't generally as crowded, though there are always a least a few people sprawled across the restaurant indulging in wings and beer.
Cumberland Brews, as is evidenced by its name, is a bar and brewery with delicious and interesting beer choices that can't be found anywhere else in Louisville. It also has a fantastic location – if you're sitting outside it's almost a guarantee that you'll see someone you know. If you're looking for a quiet place to drink and talk, you'll want to check out the top floor where the light music sets the tone for an intimate and relaxed evening. If you're hungry, try the BLT. It's one of the best in Louisville.
Flanagan's has one of the largest selections of bottled beer in Louisville and the best fries in town. During the week, Flannigan's is a laid-back and quiet place to spend an evening having conversation with friends or getting to know someone better. On the weekend, however, dance music blasts through the speakers and you can find people dancing and drinking in areas of the bar that you might have never known existed if you'd only ever been there during the week. Servers during all hours of the night mean that you can avoid standing at the bar for the most part, and a fenced-in outside area is a lovely place for drinks on warm summer nights.
Hideaway Saloon is characterized by its claim to be a hidden treasure among the sprawling stylishness of Bardstown Road -- the hidden treasure at Hideaway is that the bar is anything but a treasure. With narrow hallways, creaky stairs, and pool tables placed on barely-even floors, Hideaway Saloon embodies the definition of a hole-in-the-wall perfectly. It even has its own group of regulars, and, if you're not one of them, it can sometimes be hard to get a drink. There's occasionally a live band and sometimes a cover, but these things just seem to happen whenever they happen as opposed to with any regularity.
The Highlands Taproom is just across the street from the Mid-City Mall. There is both a downside and upside to drinking and listening to live music at The Highlands Taproom. The upside is that they showcase live bands that play solely original music every night of the week and never charge a cover. The downside is that the bar is tiny, and it's often extremely difficult to get to the bar to order a drink or to find a place to sit. However, in the summer when the deck is open, The Highlands Taproom is one of the best places to drink and listen to some of the best live music in Louisville.
Molly Malone's is an Irish pub that sits atop a green hill across the road from the Highlands' other two Irish bars, O'Shea's and Flannigan's. Molly Malone's is best visited in the summer when the deck bar is open – it is one of the best people-watching spots in all of the Highlands. At other times of the year and some weekend nights, the back area at Molly Malone's is the stage for local bands, writers, and artists. The only downside to drinking at Molly Malone's is that sometimes it's difficult to get to the bar for drinks. However, at other times there are servers who will take care of you throughout the night.
O'Shea's is one of three Irish pubs that are crowded together on Baxter Avenue just before the Bardstown/Baxter split. Like Molly Malone's across the street, O'Shea's has a very nice deck area with ample seating and lovely scenery. It's a little more secluded than the porch on Molly Malone's, so there's a little more privacy from the people walking down the street. O'Shea's has a full food menu and a large wine menu as well as a traditional bar and all of the imported beer you would expect at an Irish pub. Live bands often play there on weekends on the small stage inside.
Back in my drinking days, you could have found me at Outlook Inn on any night of the week. Though everything about Outlook looks like a hole-in-the-wall from the outside, on the inside it's anything but. The drinks are strong and cheap at Outlook, the bartenders are friendly and quick, and the crowd is diverse. It's a good place to play pool, listen to a jukebox, and just chat with friends. And with the focus on live music at most Louisville bars, being able to have a conversation in one is a thing to cherish.
The Back Door
If you think that drinking and playing pool go well together, then you'll love The Back Door. The Back Door is located on the side of Mid-City Mall opposite of Comedy Caravan. It features one of biggest pool rooms of any bar in Louisville, a game room, a kitchen with really fantastic bar food, and a full-service bar. The Back Door has really grown in popularity over the last few years – it's one of the few places you can still get a pitcher of beer to share with a group of friends. It's also a great place to go if you actually want to have a conversation with the people you're drinking with.
Wick's is well know for both its pizza and its nightlife. On any given night at the Wick's Pizza Parlor in the Highlands you'll find some sort of entertainment on the bar side of the establishment, from live music to karaoke. When I used to go out drinking a lot, I spent a lot of time with friends drinking and singing at Wick's on Sunday nights. The bartenders are friendly, it’s a great place for conversation as well as dancing and singing, and it's rare that you're bothered by other patrons of the bar.
Note: Jessica Elliott's article was edited by a current expert in March, 2016.