Oakland, the home of both University of Pittsburgh and Carnegie Mellon, gets a youthful exuberance from the flow of college students that occupy it. While the traffic on Fifth Avenue stalls and starts, Oakland itself is a dynamic, ever-changing neighborhood that makes up the East End’s beating heart. No matter where you are in Pittsburgh, you can situate yourself based on the spire of the Cathedral of Learning from Oakland, making it a grounding force. Because these neighborhoods aren’t all transplants and academics, they make for an ideal night out for both seasoned Pittsburghers and newcomers.
You’ll find poetry readings, late-night cafés and restaurants, and people of all stripes walking the streets of Oakland. South Oakland is home to some of the city’s most elegant old architecture and quirky Pittsburgh ephemera like the “Our Lady of the Parkway” Shrine of the Blessed Mother where locals claim to have seen the Virgin Mary, one of Andy Warhol’s childhood homes on Dawson Street, or the photogenic rainbow of houses on near Four Mile Run. It’s Pittsburgh’s miniature college town, and Pittsburgh isn’t Pittsburgh without it. Whether for a night out or a daytime stroll, there’s always something to do in Oakland.
A Night Out in Oakland, The Heart of Pittsburgh
Eat
The Porch
221 Schenley Drive
The Porch is a tried-and-true local staple, with bar bites and classic entrées you can depend on. Have a friend or relative in from out of town? Lunch at the porch before you visit the Carnegie Museum or the library is a great choice. Or grab a light dinner then go sit on Flagstaff Hill to watch the sunset over the city.
Butterjoint
208 North Craig Street
Butterjoint boasts a beautiful outdoor dining setup and a wide variety of shareables like goat cheese crostini, sauerkraut balls, and smoked bluefish paté, making it an ideal spot for a spring brunch with friends. But their dinner menu is also not to be overlooked, with Pittsburgh favorites like pierogies as well as a winning moules frites and Faroe island salmon.
BAO
400 South Craig Street & 114 Atwood Street
A boom of Chinese food in the East End is a rising culinary tide that lifts all boats. BAO serves up delightfully spicy chicken, noodles, and of course the titular dumplings with dim sum style table service. The vibe is comfort food and the dumplings are showstoppers, with two locations near Carnegie Mellon and Pitt respectively.
Shibam Coffee
This national Yemeni coffee chain is a popular late-night café for non-drinkers. It’s always packed, and it’s no surprise why given that they serve both strong, flavorful coffee and decadent desserts like knafe cheesecake and the recently trending Dubai chocolate bar. Shibam works as a night out nightcap, a pregame, or simply a daytime meetup spot where different cultures collide.
Drink
Spirits & Tales
5130 Bigelow Boulevard
Spirits & Tales doesn’t just have some of Pittsburgh’s best craft cocktails under the leadership of beverage director Amnelis Cruz—it also has one of the city’s best views. On top of the Oaklander, you can see far into the hills, riverbanks, and bridges of the entire city of Pittsburgh while enjoying brasserie food and top-notch beverages. For anyone visiting, The Oaklander is also an unbeatable hotel for its classy flair and central location.
Bootleggers
403 Semple Street
The side streets leading into the much more residential South Oakland are easy to lose yourself in, with dramatic hills and a mixture of student housing and dyed-in-the-wool generational Yinzers. Bootleggers is the spot for people in that part of the neighborhood who don’t want to venture too far towards Forbes. Open until 2AM, it’s a good casual date bar or catch-up spot with friends.
P*Town
4740 Baum Boulevard
On the edge of Oakland and Bloomfield, P*Town is a gay bar that calls itself “a Cheers like bar for the community.” It gets its name from the idea that Pittsburgh is a big city with a small town feel, with a welcoming, friendly vibe for anyone. If you’re looking for drag nights, comedy, and karaoke, this is the spot.
Hemingway’s
3911 Forbes Avenue
Hemingway’s is right between Pitt and Carnegie Mellon, at the busiest point in Pitt’s campus, so…it’s always bustling. They host a multi-week poetry reading series throughout the spring months, founded by poet Jimmy Cvetic in 1974 and now stewarded by Kristofer Collins and Joan Bauer. The food is casual and inexpensive, the vibes are homey, and the pours on the drinks are generous. What more could you want?
Culture
Carnegie Museum of Art, Carnegie Museum of Natural History, & Carnegie Library of Pittsburgh
One building holds three of Pittsburgh’s most important cultural institutions. At 4400 Forbes Avenue, you can see two museums for the price of one, with hands-on activities for kids and engaging cultural programming for adults. There really is something for everyone in this building. There’s history through the Hall of Architecture and the museum’s permanent collection, a robust contemporary art program in the Forum Gallery and Heinz Galleries, and even tasty snacks at Yinz Coffee and Café Carnegie. The Carnegie Museums are one of Pittsburgh’s crown jewels, and the Thursday night late hours make for a great jumping-off point for a night out.
Cathedral of Learning
4200 Fifth Avenue
In Michael Chabon’s Mysteries of Pittsburgh, the protagonist looks out over the “bottom of Pittsburgh” and thinks to himself: “I made a sudden, frightened vow never to become that small, and to devote myself to getting bigger and bigger and bigger.” It’s the quintessential youthful angst, and I think about it every time I get to see the 360 view atop the Cathedral of Learning. Entry is free to wander the gothic halls, look at the nationality rooms, and find yourself at the 36th floor for views of Schenley Park and the skyline of downtown where you, too, can ponder your smallness.
Phipps Conservatory
1 Schenley Park
During the winter, Pittsburgh is lacking in color. Phipps, at the edge of Schenley Park, is the place to find it. No matter what’s happening outside of the conservatory glass, Phipps remains beautiful and blooming, making it one of the most comforting places in Pittsburgh. On Fridays, it’s open until 10PM for late night strolls through the orchids, bonsai, and cacti under the dazzling greenhouse lights.
Caliban Book Shop
410 South Craig Street
Caliban Book Shop is like the Platonic ideal of a used bookstore. Books pack the shelves to the brim, with only narrow passageways in between them. Looking for an occult spellbook? A transcription of spoken word poetry? An academic tome about the history of Italian Jews? Caliban has anything and everything, with a curated, eclectic selection. They’re also open until 8:30 on Thursdays to match the museum’s late night hours.
Take a look at the rest of our neighborhood night out series:
- A Night Out in Sharpsburg, A Gem Just Outside of Pittsburgh
- A Night Out in Lawrenceville Is Never Boring
- Downtown Pittsburgh’s Best Bars and Restaurants for Happy Hour and Beyond
- Saturday Night on the Hilltop
- A Night Out on the South Side Beyond the Dive Bars
- A Night Out on the North Side, Not Just Stadium Food
- A Night Out on the East End, Part One (Bloomfield, Garfield, Highland Park)
- A Night Out on the East End, Part Two (Shadyside, Squirrel Hill, Point Breeze, East Liberty)
- Plan A Night Out in Wilkinsburg, Edgewood, Swissvale, & Regent Square
- Find the Unexpected on a Night Out in Sewickley, Emsworth, and Bellevue
Story by Emma Riva
Photo courtesy of Oakland Business Improvement District
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