Pittsburgh’s Southside is like that aging actress who never quite figured out how to put down the bottle.
Full of the grace and beauty that come naturally with well preserved, century old buildings but never quite having grown out of its punk rock upbringing, she screams class all the day long, but the stains of last night’s chug line still yellow her fancy white dress.
None of this is meant to chastise the neighborhood. It’s home to more than one excellent sushi place, a local blue jeans company (how often do you hear of that?), the city’s legacy coolest coffee shop and more great bars and restaurants than a Hawaiian phone book. A bicycle path, the Three Rivers Heritage Trail, winds along the southern banks of the Monongahela River, through Southside’s Riverfront Park and into the remnants of the neighborhoods industrial zone, leading to the Southside’s famous Station Square, a former train depot which now serves as home to countless chains like Joe’s Crab Shack and a mall where you could purchase enough black and gold sports memorabilia to outfit the entire Steeler Nation.
If you’re the touristy type, Station Square is probably where you’ll want to start in Pittsburgh. It’s a healthy combination of the fat of big business gone wild, local history and nightlife fiasco that’s sure to keep middle aged women, Rust Belt buffs and old enough to drink but not old enough to party with their tops on ladies satisfied. It’s also a transportation hub. You can hop on the “T”, Pittsburgh’s light rail service that will shuttle you across the Mon River via bridge to downtown’s short few blocks of underground subway, or head south into the city’s more “real” neighborhoods, where yinzers, an endearing term for locals based on a common Pittsburghese term for “you all”, which locals have somehow shortened to “yinz” over the decades. I rode the T for a year while working for a now defunct coffee shop in the subway, and it’s a gloriously smooth ride that leaves one wondering why public transportation in the form of shaky, crowded buses exists at all. Of course, you can catch one of several buses here that’ll take you anywhere in the city you need to go. Or hop on the aforementioned bike path and get your traveling done with a dose of exercise along the way.
But the most beautiful form of transportation available from Station Square are the inclines. Inclined planes are essentially short trains that ride their track up the sides of cliffs. They’re almost unique to Western Pennsylvania, from my understanding, and the most easily accessible one from Station Square—the Monongahela Incline—provides hike free access to Mt. Washington, one of Pittsburgh’s least visited but coolest, most impressive neighborhoods, and in particular Grandview Avenue, one of the rare chances you’ll have to stand on a cliff and look down at a city’s skyscrapers from above. Considering that Pittsburgh has an impressive skyline—though the downtown area is small, it boasts a tower made nearly completely of steel and a similarly nearly all glass castle—the dollar-and-some-change fare you’ll pay for the ride is well worth it.
At the other end, Southside’s eastern edge, lives a fairly new outdoor mall full of Cheesecake Factories and H&M stores alongside REI and a massive movie theatre, peppered with a few local restaurants and a public park where children can get their summer selves completely soaked in a fountain or play life-sized chess on a board just north of the complex. Bicyclists can hop on the Hot Metal Bridge from there and continue on to Three Rivers Heritage Trail to downtown or make a steep climb up Bates Street into Oakland, the city’s “second downtown”, home to the University of Pittsburgh and a menagerie of hospitals, college dives and the homeless living alongside businessmen and the next generation of America’s workforce.
These two chain store havens are like the cheap white bread used to house a sandwich full of organic turkey, though. The main drag of Southside, East Carson, is practically made of 100% Pittsburgh-grown businesses. Piper’s Pub offers football—that is, soccer—within a traditional Scottish pub experience. The Beehive is a testament to longevity, one of Pittsburgh’s oldest and hippest coffee shops, even with Starbucks having moved in across the street years ago. Dee’s Pub glows neon and boothes hipsters flaunting their PBRs on one half of the bar, while a traditional jukebox full of punk rock favorites rattles the pool tables of the opposite room. There’s a Primanti’s, there’s Thai, Japanese, and Philly cheese steaks. Tattoos? Try any of about a bajillion options. Tobacco shops, churches and what must have been one of the first Burger Kings ever all live in one neighborhood. Ten or fifteen years ago, this was the cheap, hip neighborhood. Now it’s the expensive, only slightly less hip place to be. Just be aware that as of happy hour, the alternative crowd proving that they can get as drunk as the frat boys in Oakland will be puking, pissing and partying their way down the street in abundance. And getting a cab at 2am when the bars let out? You might as well just start walking now.