By Jessica Wasik
Pittsburghers love their city, their sports teams and, of course, their bars. Whether that be a laidback dive bar or an upscale lounge, the city is bustling with boozy hangouts. Narrowing down the best of the best can certainly be challenging, but there are some that have stood the test of time for decades. Here are the city’s five most iconic bars worth checking out during your next night on the town.
1117 E. Carson St.
Pittsburgh, PA 15203
As the South Side’s oldest bar, Jack’s Bar has become a legendary watering hole in its own right. Low-priced drinks, gigantic pitchers of liquor and awesome bar bites are just some of the reasons this iconic bar has consistently been named among the best in the South Side. You can’t miss its rainbow-colored glass block front and eye-catching neon lights that beckon you inside where you’ll find an eclectic mix of patrons, ranging from college students to white collar businessmen. Jack’s Bar is conveniently located on East Carson Street, making it the ideal spot to kick off a bar crawl or nightlong celebration.
3117 Brereton St.
Pittsburgh, PA 15219
If you love a good dive bar, you’ll appreciate the atmosphere of Gooski’s. Locals know this is the place to go for everything from cheap drinks to what are rumored to be among the best wings in Pittsburgh. Entertainment often ranges from ping-pong to punk rock with exceptional service by Gooski’s staff. Throw back a few at this Polish Hill bar that promises a what-you-see-is-what-you-get vibe.
1114 Grandview Ave.
Pittsburgh, PA 15211
There are few better places to really wow your date than at the LeMont Lounge, noted as one of the city’s best upscale bars. With its incredible view of the city skyline paired with unmatched drinks, you’re guaranteed to have a memorable evening. Piano music is a relaxing way to ease into the night as you dine on a menu featuring favorites like colossal shrimp cocktail, raspberry duck and New York strip steak complete with wine or cocktails. The LeMont Lounge is located within the celebrated LeMont Restaurant on Mount Washington.
Related: Best Bars With History In Pittsburgh
1372 Freeport Road
Pittsburgh, PA 15238
There’s just something about Bob’s Garage that gives off a little extra shine. Perhaps it’s all the decorative twinkling strings of light that stay lit year-round and help put you in the spotlight during its iconic karaoke nights. With a neighborhood feel, Bob’s Garage is nothing fancy; it’s simple a go-to for good drinks, great service and a fun night out. Whether it’s your first time performing your favorite karaoke hits here or you’ve earned recognition as the bar star, everyone is made to feel welcome here. Grab your gang and hang at Bob’s Garage, located in Blawnox.
Omni William Penn Hotel Speakeasy
530 William Penn Place
Pittsburgh, PA 15219
To step into the Omni William Penn Hotel’s Speakeasy is to step back in time to a period in local history reminiscent of 1920’s Pittsburgh. Even to many Pittsburghers, the Speakeasy remains a hidden gem, but one well worth seeking out for its iconic Prohibition Era atmosphere and unique drinks alone. Inside you’ll find an amazing collection of 1920’s memorabilia, including antique whiskey bottles and old seltzer bottles, many of which still function. Experience a one-of-a-kind watering hole by visiting this historic refurbished speakeasy within the Omni William Penn Hotel.