The Newcomers Guide to South Side | City Guide | Pittsburgh | Pittsburgh City Paper

The Newcomers Guide to South Side

click to enlarge The Newcomers Guide to South Side
CP photo: Jared Murphy
Doce Taqueria
When the sun goes down on any given night of the week, South Side’s main drag turns into one massive bar crawl. You’ll find everything from old-school drinking holes like Dee’s Café ( with its cheap beer and pool tables, to Acacia (, a cocktail bar designed in Prohibition-era style. But while this neighborhood stays up late, the daytime can be just as fun. Start your morning off right with a coffee from Big Dog Coffee ( or a sweet treat from The Milkshake Factory (, with over 50 flavors of over-the-top delicious milkshakes. Take in a movie and some shopping at SouthSide Works (, an entertainment complex where you’ll find a multi-screen theater and popular chains like REI, Urban Outfitters, and The Cheesecake Factory; plus, an outdoor riverfront area where you’ll find bike rentals and concerts during the summer.

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Arts + Culture

Black Forge Coffeehouse ( is actually about a mile up the road from South Side in nearby Allentown, but worth a mention. It’s more than just a coffeehouse, offering art installations, heavy metal performances, poetry, and jam sessions. The coffee’s good too! After you’re caffeinated, scoot over to Onion Maiden ( for some of the world’s best all-vegan comfort food and a great pun-filled menu.

City Theatre ( is a long-standing theater group offering a regular slate of contemporary plays, including those with topical, political, or off-beat themes.

Bring your friends and family for an adventure game inside a room that’s an interactive puzzle. At Escape the Room PA (, you can find clues to help you escape in 60 minutes.

click to enlarge The Newcomers Guide to South Side
CP photo: David Heath
Rex Theater


From folk to jazz to funk and more, Club Cafe ( is a gem just off East Carson Street. It’s a great place to catch local music and comedy, as well as gigs by national touring acts.

Rex Theater ( is a larger-capacity venue housing an impressive variety of shows. Rock acts, comedians, freak shows, and storytelling nights all find a home here.

With early all-ages shows upstairs and 21-and-older gigs later in the evening on both floors, The Smiling Moose ( is a versatile place to catch a show. And the food is awesome.


Smothered chicken and waffles, a side of greens, and a bowl of fish stew. Pretty much anything you try at Carmi Soul Food Restaurant ( will be satisfying. This new location, recently moved from its longtime spot on the North Side, now offers cocktails and live entertainment.

Doce Taqueria ( has the tacos you crave — from basic (meat, lettuce, cheese) to more off-beat specials. Low prices mean you can order plenty.

Double Wide Grill ( is an open, dog-friendly bar inhabiting an old gas station. It’s a great place to meet a group of friends for some grub and beer. It also has great vegan and veggie options.

Ride your bike to Over the Bar Bicycle Cafe ( for a pint and some pub fare to fuel you up for the road.

Piper’s Pub ( is a British Isles-inspired pub, with whiskey, beer, scotch eggs, and Euro football on the telly. Next door is the Pub Chip Shop (, for savory pies and donuts.


Highway Robbery ( is a treasure trove for finding awesome vintage clothes and accessories, and the expert curation makes it feel like fun instead of work.

Famous musicians are known to stop in to check out the merchandise at Pittsburgh Guitars ( for good reason. It’s locally owned and the staff knows their gear. In addition to new and vintage guitars, the shop also sells amps, accessories, and an impressive selection of ukuleles.

Long live independent bike stores! With super helpful staff and a nice selection, Thick Bikes ( will help you acquire a new bike, fix your old bike, or snag a new helmet and riding gear at a reasonable price.

Where the Locals Go

Fun fact: South Side is technically two separate neighborhoods: South Side Flats (where the bars are) and the residential South Side Slopes (the houses on the hill). How do people get around on that massive hill? Public steps! Pittsburgh has more than 45,000 steps, and the Slopes contain more than 10 percent of those. Locals hit the steps for exercise and unique city views. Take a walk up the hill after you’re done stuffing your face in the Flats; or, join StepTrek (, a yearly venture taking visitors on a hike of more than 2,000 of those stairs, totaling over seven miles of urban exploring. (We just don’t recommend doing so after bar crawling.)