Article Updated April 13, 2026 by Lauri Gravina

One of Pittsburgh’s most bustling city neighborhoods, Oakland is the epicenter of our renowned eds and meds communities, with three universities and four hospitals. But this city within a city is also a dynamic place to explore.

With more than 44,000 students, there’s a youthful exuberance from the flow of college students walking and hanging out at Schenley Plaza. Let’s take a note from them: this city neighborhood is best negotiated by foot, so park your car and set out to see what Oakland has to offer. You’ll find museums, libraries, architecture, late-night cafes, international food carts and restaurants, bookstores, and people of all stripes walking the streets.

Here are just a few stops to get you started.

A Night Out in Oakland, The Heart of Pittsburgh

Eat

The Porch

221 Schenley Drive

Truly a place that every Pitt parent knows, The Porch is a tried-and-true 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 museums and library is a solid choice. Their wings are a winner, as are the Brussells sprouts, each having a crispy bite.

The menu isn’t too big or too small — and has something to please most. Generous salads, like the Thai peanut shrimp with fried wontons peanut sauce; there are five pizzas, and a truffle or veggie burger. Porch Plates include salmon, sea bass, steak, and roasted red pepper chicken. Their happy hour is 4 to 6 pm weeknights and on weekends, they also serve brunch, including house made buttermilk biscuits with fennel sausage gravy. The restaurant sits alongside the park-like Schenley Plaza, so gives patrons a nice respite from the city buzz — plus, they have a pretty nice porch.

Butterjoint

208 North Craig Street

Patrons might go to Butterjoint in search of one of the city’s best burgers (think Gruyère cheese, bacon, smoked pepper aioli, and sour dill pickles) but there is so much more to the popular spot, which in the warmer months offers ample outdoor seating. The menu is inspired, serving tasty Japanese bread rolls served with apple butter (called “lumps”), a smoked bluefish pâté, sauerkraut balls, and goat cheese crostini made with Goat Rodeo chèvre. Butterjoint also serves a winning moules frites, Faroe Island salmon, and Pittsburgh faves like pierogies with sausage (kielbasa, caramelized onion, caraway kraut, and pickled beets.)

BAO

400 South Craig Street & 114 Atwood Street

A boom of Chinese food in the East End is a culinary tide that remains strong, elevating all boats. Taiwanese-influenced BAO serves up delightfully spicy chicken, noodles and is the only local places to order fried turnip cake, a dish made from shredded daikon radish, rice flour, and Chinese pork sausage. The handmade dim sum offers a broad range of dishes — and the dumplings are showstoppers. There are two locations near Carnegie Mellon and Pitt, respectively.

Shibam Coffee

This national Yemeni coffee chain is a popular late-night café for non-drinkers. The organic beans are handpicked in the Yemeni highlands and deliver a spicy sweetness to the brews. A variety of teas are also available, including the Adeni tea, a Yemeni black tea simmered with cardamom and milk. With their deeply flavored coffee and dessert menu, Shibam pulls in the patrons — it’s always packed. Try the milk cake, a soft cake soaked in three milks and whipped cream, or the sabaya, a flaky, layered Yemeni pastry served with honey. 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

Located on the top floor of the Oaklander Hotel, Spirits & Tales doesn’t just have some of Pittsburgh’s best craft cocktails, it also has one of the city’s best views, extending to the hills, riverbanks, and bridges. With an elegant feel draped in French Blue decor, Spirits & Tales is a winner of spot to take visitors and show off our city as you sip a cocktail, like the Velvet Fig, made with Ketel One vodka, allspice syrup, fig preserve, and lime. The brasserie is open for breakfast, lunch, and dinner. Dishes include a cassoulet — with a duck leg, pancetta, sausage, and navy beans and pomegranate — as well as a dish not often seen on menus: dauphinoise potatoes, a classic French comfort food.

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.” Named for “Pittsburgh Town” to celebrate our big city with its small-town feel. It’s more than just a bar — the gay night club is a nightlife mecca with a vibrant dance floor, a pool table, and a full roster of fun including karaoke, drag shows, and open mic nights. Know that they don’t serve food, but patrons are welcome to BYOF (many people order in pizza from down the street).

Hemingway’s

3911 Forbes Avenue

It’s final call for Hemingway’s, as the long-standing college haunt closes its doors on May 3, 2026. So, be sure to make your last stop to the bar and restaurant that is known for its decades-long poetry series, serving beers and cocktails by the pitcher, and having a sometimes salty waitstaff. The booths and tables start filling up early, as students stop for jalapeno poppers and nacho tots to end their day of classes. Cheers to the memories!

Culture

Carnegie Museum of Art, Carnegie Museum of Natural History, & Carnegie Library of Pittsburgh

Oakland is home to three of Pittsburgh’s most important cultural institutions — and they’re all located under one decidedly large roof. Visitors can tour both the Carnegie Museum of Art — with its Halls of architecture and sculpture and many galleries — and the Carnegie Museum of Natural History — with its unrivaled Kamin Hall of Dinosaurs, its stunning Hillman Hall of Minerals and Gems, as well an exhibit that examines indigenous cultures around the county. The Café Carnegie offers a menu of light, refreshing dishes, Commonplace coffees, and a full bar. Also be sure to check out the famed Carnegie Public Library, which opened in 1895. There really is something for everyone in this building, and the Thursday night late hours make for a great jumping-off point for a night out.

Cathedral of Learning

4200 Fifth Avenue

The Cathedral of Learning is an architectural masterpiece that simply should not be missed. Reaching 42 stories, the Gothic Revival skyscraper dominates Oakland’s skyline — but be sure to step inside. You will marvel at the Cathedral Commons, a four-story room that looks like Pittsburgh’s version of Hogwarts Castle.

Be sure to check out the museum-caliber Nationality and Heritage Rooms — it’s an education in history, geography, anthropology, art — and Pittsburgh — all wrapped in 31 rooms. Each room is dedicated to a different country and tells the stories and cultural histories and customs of some of Pittsburgh’s earliest immigrant populations. The gift store is stocked with imported wares, such as brightly painted Turkish pottery, Scottish plaid wool scarves, handmade sake sets, Korean skin care, and evil eye magnets. While in the Cathedral, you can even make the trek — or take the elevators — to the top for views of Schenley Park and the city skyline.

Phipps Conservatory

1 Schenley Park

Truly one of Pittsburgh’s brightest and most colorful spots, a visit to Phipps will most assuredly elevate your mood and enrich your spirit. The Victorian greenhouse opened its doors in 1893 with the intent to be a source of “instruction and pleasure to the people.” The conservatory offers an array of environments, from desert to tropical forest, from a conservatory dedicated to bonsai to a Japanese courtyard garden, from a room dedicated to orchids to Phipps’ grand foyer featuring the chandelier made by esteemed glass artist Dale Chihuly. Plus, there are events to celebrate every season. The gift shop is rich in texture and colors and offerings — glass flowers, houseplants, handmade home décor, dried wreaths, and unique jewelry — that is sure to delight a botanical lover’s soul. On Fridays, Phipps is open until 10 pm for evening strolls through under the dazzling greenhouse lights.

Caliban Book Shop

410 South Craig Street

Opened in 1991, Caliban Book Shop is like the Platonic ideal of a used and rare 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. The basement is stacked with paperbacks, mysteries, and science fiction, all priced well under retail. Shoppers can also sort through their vinyl records corner, which focuses on Indie Rock, Sixties pop, Americana, and punk albums. Caliban is open 7 days a week, and until 8:30 on Thursdays to match the Carnegie 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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