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.
O'Shea's
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.
Outlook Inn
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.
Phoenix Hill
Phoenix Hill Tavern is Louisville's oldest nightclub, located at the corner of Baxter and Broadway. The two-story club houses five different bars, each offering a different type of music or entertainment. Three of the bars showcase live, local bands every weekend -- typically cover rock bands in the Saloon and Roof Garden and acoustic, original bands in the Taproom. Both the Roof Garden and the Saloon also occasionally have headliner concerts. Phoenix Hill's Deck Bar is filled with DJ-played dance music. The front of the club houses a karaoke bar and diner.
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 Pizza Parlor
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.





