One Night Out in … Pittsburgh, Pennsylvania

Where to eat, drink and party if you've got one evening in the Steel City

November 13, 2019 6:15 am
Cocktail from Butcher and the Rye
Elyssa Goodman for InsideHook

This is One Night Out, a series in which we deliver you marching orders for the perfect vacation in cities around the world with one caveat: you’re only planning to be there for one night.

In 2006, I had been living in Pittsburgh as a college student for two months when the actress Sienna Miller had proclaimed the city “Shitsburgh,” unleashing the fire and brimstone of some two million people across the area. Even as a months-long resident I was offended and found the sentiment unwarranted, unsubstantiated and untrue: in all of its charms, the city had grown on me to that point. I loved its cultural offerings, its proliferation of museums and galleries, its mom-and-pop businesses, its quirky shops, its brilliant restaurants, its walkability, and more. There are few cities I’ve been to or lived where residents love their town as fiercely as Pittsburghers do, let alone a near-pathological love for the Pittsburgh Steelers that leads many to call the city “a drinking town with a football problem.” 

And even though such a moniker is deeply true — when the Steelers won the Super Bowl in 2009, I remember hearing a massive, collective roar emerge from the Oakland neighborhood near the University of Pittsburgh, where couches were later set on fire and a bus shelter was smashed into oblivion, all in the name of joy — it doesn’t detract from the other thrills the city has to offer. Far from shitty, Pittsburgh contains multitudes. Though it’s not necessarily like “destination” locales in Miami or New York, Pittsburgh is regularly named “America’s Most Livable City.” It’s close to water, cosmopolitan, affordable. What’s not to love? Any opportunity I have to go back brings me joy. 

Pittsburgh’s gritty Rust Belt reputation has grown new, urbane roots across its 58 square miles in the last few years. And though it’s still a smaller city, more on the scale of Cincinnati than San Francisco, it’s still one that’s ripe with cultural capital. Even in one night out there, you can get a taste of life now and in the past, whether you’re in a top-notch museum, stylish, James Beard-nominated cocktail bars and restaurants, a hipster dive bar, a raucous hip-hop party, or an old-school Pittsburgh diner. “Nothing is boring except to people who aren’t really paying attention,” Pulitzer Prize-winning novelist Michael Chabon wrote in his 1988 book The Mysteries of Pittsburgh. So pay attention to the city. You’ll be glad you did. 

Good Fridays at The Andy Warhol Museum (117 Sandusky St, Pittsburgh, PA 15212)

Warhol himself is a native son of Pittsburgh, a longtime resident of the Oakland neighborhood and an alumnus of Carnegie Mellon University (then Carnegie Tech…full disclosure, I’m a little biased as I attended CMU myself). Every Friday, The Warhol stays open later into the evening, until 10pm, and offers reduced admission and a cash bar. The minimalist space, with its white walls and concrete stairs, lets Warhol’s colorful works shine. When I’m there, his famed 36-foot silkscreen Elvis (Eleven Times) makes its home on an entire wall, the King in various shades of black against a silver background. And while the portraits of Mick and Liz are always fun to see, not to mention the occasional Haring and Basquiat, you can also shoot your very own Warhol Screen Test just like Dalí and Dennis Hopper did for Andy himself back in the day (here’s mine, and here’s one by famed artist Ai Weiwei). Sitting right in front of an old-school Bolex camera, you get to feel like a movie star, a Factory star, or both, plus it’s shot digitally and minutes later it’s in your inbox. On a different floor, it’s never not fun to play with Warhol’s Silver Clouds, the constantly floating rectangular silver balloons ripe for a selfie — fun fact, the Silver Clouds room has a door that leads to a small room with a helium tank in it. When I was there, the door was open and someone was refilling the balloons and I felt like Dorothy peeling back the curtain on the wizard of Oz. There’s also a Chelsea Girls exhibition on right now, and you can sit down and watch it for as long as you’re able, physically and/or mentally. While the film is notoriously difficult to sit through, I was there with a friend who had not just seen it but projected its many reels and screens four times, so if he can do it, you can surely swing a few minutes. And in the basement, there’s an old-school black and white photobooth that mimics the pictures Warhol used for screenprints. I once seduced someone in there! Maybe you can, too. 

Butcher and the Rye has a lot of whiskey (Elyssa Goodman for InsideHook)

Butcher and the Rye (212 Sixth Street, Pittsburgh, PA 15222)

The first thing I see upon wandering into Butcher and the Rye in downtown Pittsburgh is an array of suits. The craft cocktail bar — the first one in Pittsburgh nominated for a James Beard Award —  looks like the idea of a modern gentleman’s den brought to life in 2019, but without the misogyny. There’s butcher paper on the walls detailing specials, a two-story high bar with an array of whiskies eight shelves long and four wide. It’s accented by an enormous chandelier of exposed lightbulbs, forestry-printed wallpaper, and an occasional taxidermy surprise (a fox wearing sunglasses carrying a pheasant in its mouth, for example). Sitting down at my marble-topped table in the restaurant’s Rye Bar, on its top, third level, there’s the sound of cocktail shakers in the distance at the downstairs bar below me. The simpler cocktails are made there, the waiter tells me later, the classics, the ones with fewer ingredients. But the more complex ones are made up here, can only be ordered up here (unless you ask nicely, of course), and take a little longer. I ease into the Glendale Glow (Knob Creek Bourbon, Tea Mulled Wine Reduction, Lemon, Vigo Amarone), because how could I come to a bar like this and not order brown liquor of some kind? It’s fruity and smoky and tastes like fall but not in a basic way. I sip slowly as Rihanna and Ne-Yo purr through the speakers. Later, I’m tantalized by the Maokong Mist (Oolong-infused Ardent Union Vodka, Dolin Dry and Blanc Vermouths, Matcha Powder, Honey, Lemon, Cream). Yes, it’s a vodka drink, but the bar actually infuses all of their own vodkas, and makes their own juices, shrubs, and syrups. Sipping the Maokong in all of its creamy, matcha-y goodness from a large, elegant coupe, it’s a cocktail I’m sad to see go…so much so that I almost attempt to lick the interior of the glass. 

The Grass-Fed Beef Tartare at Legume with a wobbly egg yolk is utterly decadent (Elyssa Goodman for InsideHook)

Legume (208 N Craig St, Pittsburgh, PA 15213)

At Legume with my friends Hannah and Jeff, Pittsburgh locals, we’re greeted by warm light and friendly staff who seat us at a wooden table that’s somehow both elegant and casual. Those are incidentally great words to describe Legume, a Pittsburgh staple for 12 years and semifinalist in the 2018 James Beard Awards’ Outstanding Restaurant category. We sip cava from long, lean flutes, each toast sparkling. As the courses arrive from the seasonally changing menu, our eyes widen and we pray for more room in our stomachs. The grass-fed beef tartare with a wobbly egg yolk is utterly decadent — photographing it is a little sexual, I say with a laugh. “Is this your Georgia O’Keefe moment?” Hannah chuckles. Of similar meaty perfection is the chicken liver mousse with stanley plum jelly, together salty and sweet. The turnip and apple soup with duck confit is a light, creamy dream. Entrees are next, with an exquisite sweet potato ravioli I can taste even sitting writing this right now in all of its brown butter glory; beer-braised beef chuck that’s magically tender with an ever-so-slight crust; and a duck leg confit that’s so good Hannah quips it “makes chicken look like food for paupers.” Jeff does his best impression of David Duchovny’s J.P. Prewitt in Zoolander, hand modeling each dish like his life depended on it. We take turns nibbling each dish, passing them in a circle until there’s nothing left. I miss each of the entrees when they’re gone. 

Brillobox is keeping it weird in Pittsburgh (Elyssa Goodman for InsideHook)

Brillobox (4104 Penn Ave, Pittsburgh, PA 15224)

Brillobox is in Lawrenceville, a neighborhood which used to be a hipster heaven but Hannah informs me that “all the mustache wax places have already closed, you know what I mean?” The flannel crowd may have traded beanies for babies, but Brillobox remains cool, “keeping it weird since 2005.” There’s an Elvis cookie jar adorned with hoop earrings above the bar, an oversized shark on the wall with a Donald Trump mask being chomped in its jaws, shiny red booths, a deer head adorned with wreaths of faux fall leaves and Christmas lights, a pink elephant sculpture and neon playing cards flickering on the wall, and a projector rocking the terrible 2018 Nicolas Cage movie Mandy (I discover what it is by quickly Googling “nicolas cage crossbow movie” in my phone). Sitting at the dark bar, tattooed bartenders pour us inexpensive but tasty cocktails and beers before we head upstairs to The Red Room. That space plays host to a variety of events, often dance parties like tonight’s Union event, $10 at the door, featuring rad hip-hop from DJs Big Phill, Selecta, and Blakk Steel. Men wear fire sneakers and women swivel in stilettos to everyone from Biggie to Snoop to Fat Scoop. “You got a ten dollar bill, get your hands up!” and I throw my hands joyfully in the air as “Be Faithful” blazes through the speakers. The blue ceiling is covered in silver glitter that sparkles with lights from the stage, and walls are covered in red and polka dots. Soon we’re a sweaty mess in a sea of bodies that are also sweaty messes and it’s brilliant. There are few better ways to spend a Friday night than covered in sweat and hip-hop. 

Winding down at Ritter’s (Elyssa Goodman for InsideHook)

Ritter’s (5221 Baum Blvd, Pittsburgh, PA 15224)

As the clubs and bars close in Pittsburgh for the night (around 2-3am), you may find yourself jonesing for a snack. Look no further than Ritter’s, beloved in the city since 1951, and in its current location since 1975. It’s open 24 hours on Thursdays, Fridays, and Saturdays, one of the few in the Pittsburgh area. Co-owner John Velisaris mentions it can get a little rowdy at that hour, but emphasis on little. He jokes that the college kids who frequent at that hour come back after graduating years later and say “I’ve never seen this place during the day!” It turns out yours truly is among them. But how could I forget the diner’s signature jukeboxes on each table, thick ceramic plates that clunk against the countertops, the refrigerator full of pies topped with luscious berries and whipped cream, the waitresses in brightly colored cardigans who call you honey and don’t judge you too much when you order poached eggs on toast with cheese like I did (breakfast is 60 percent of their business, Velisaris says, though he also says you can’t go wrong with an omelet). If you sit at the counter, with its delightfully swiveling stools, you might even be lucky enough to hear locals chatting in that famed Pittsburghese accent n’at, ya jaggoff, then head dahntahn to fall blissfully asleep. You may even get to see a gorgeous Pittsburgh sunrise before you do.

Related: How to Have a Perfect Night in Ft. Lauderdale


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