A guide to Pittsburgh: Things to do in Oakland

Oakland is often seen as home to UPMC, the University of Pittsburgh, Carnegie Mellon University and Carlow University – but it is so much more. Old meets new as its rich neighborhood history shines through in the architecture of buildings and homes, while new developments make it a destination for medicine, education and research.

The city neighborhood is comprised of North Oakland, South Oakland, West Oakland and Central Oakland – although North and South are the now well-known areas.

The neighborhood has made headlines over the past few months because Walnut Capital proposed a large development near the Boulevard of the Allies called Oakland Crossings. Some residents are none too happy, even though the proposal calls for a grocery store, green space and a pedestrian bridge over the boulevard. Pittsburgh Mayor Ed Gainey asked Pittsburgh City Council for a 30-day break on the project’s proposed zoning ordinance.

“I am hopeful we will find a solution that prioritizes equitable development, aligns with the priorities raised by residents in the Oakland Plan process and delivers on much-needed affordable housing prospects for the people of Pittsburgh,” Gainey said.

Regardless of the outcome, Walnut Capital’s interest in the area is proof that development and interest in Oakland will continue.

Here are some things to check out:


Carnegie Museums: Two out of the four Carnegie Museums call Oakland home – the Carnegie Museum of Natural History and the Carnegie Museum of Art The price of admission includes access to both museums. The history museum opened in 1895 and is home to real dinosaur skeletons, the Wertz Gallery of Gems and Jewelry, the Paleolab, the Hall of Botany and much more. Founded in 1896, the art museum is one of the country’s first contemporary art museums and includes more than 30,000 objects in various media. It was originally located in what is now the main branch of the Carnegie Library of Pittsburgh. Both were funded by steel baron and philanthropist Andrew Carnegie.

Cathedral of Learning: The Gothic Revival skyscraper that the University of Pittsburgh Chancellor John G. Bowman commissioned in 1921 did not break ground until 1926 and was not officially dedicated until 1937 – but, the first class was held in the incomplete building in 1931. A $ 10 million price tag was offset by donations from the public and local school children. A 10 cent donation got students a certificate stating that they were “Builders of the Cathedral of Learning.” At 40 stories and 535 feet tall, it was the world’s tallest academic building when it was built. Today, that honor is held by the main tower of Moscow State University in Russia. Many of its 31 Nationality Rooms hold classes, a stunning Commons Room is a place to both study and socialize, and offices, libraries and computer labs are also housed in the building.

Heinz Chapel (South Bellefield Avenue): Just across the Cathedral of Learning’s lawn sits the famed and beautiful Heinz Memorial Chapel. It was dedicated in 1938 and does not belong to any religious denomination. It hosts about 1,000 events per year – but if you want to get married there, you should book early. Time slots can be reserved for two years in advance, but they fill up fast.

Tribune-Review file photo

The old wall from Forbes Field in Oakland.

Forbes Field Outfield Wall: (Roberto Clemente Drive) While the final baseball game at Forbes Field was played on June 28, 1970, pieces of it remain on Pitt’s campus. Portions of the outfield wall are still standing off of Roberto Clemente Drive (it runs from Schenley Drive to South Bouquet Street behind Wesley W. Posvar Hall).

Inside of Wesley W. Posvar Hall, the home plate is located under protective glass on the first floor.

Schenley Park: A destination park in Pittsburgh with hiking trails, biking, a golf course, an ice skating rink and an overlook of the skyline.

Soldiers & Sailors Memorial Hall & Museum: (4141 Fifth Ave.) This building houses the largest memorial in the US dedicated to the military. Inside is a 2,500-seat auditorium and a banquet hall.

St. Paul’s Cathedral

Petersen Events Center: (3719 Terrace St.) Known as “The Pete” this 12,500-seat arena hosts Pitt men’s and women’s basketball, concerts and other university functions.

Food & drink

Butterjoint (214 N. Craig St.): This former burger joint has evolved into a more eclectic menu. Still, burger selections and a pierogi plate remain on the menu.

Dave & Andy’s: (207 Atwood St.) On warm spring and summer days, it’s not uncommon to see this line wrapped all the way around the block to get into Dave & Andy’s for their amazing homemade ice cream. The rotating flavor menu includes birthday cake, oatmeal cream pie, white haus and white chocolate cinnamon habanero, in addition to the standard chocolate, vanilla and more.

Fuel & Fuddle: (212 Oakland Ave.) This Oakland gastropub featured an array of microbrews before microbrews were a thing. Today, it boasts 10 beers on tap and 100 in bottles or cans. The food menu is pub grub with a twist – and it hasn’t changed much over the years. Warm up with a bowl of Rosa’s chipotle chorizo ​​chili or try one of the “live fire pies.” Sandwiches and burgers come with a mixture of russet and sweet potato fries. And while it’s not new, the “bat outta hell” housemade meatloaf dinner with smashed redskin potatoes and herb gravy is a fitting tribute to a musical legend.

Hemmingway’s Cafe: (3911 Forbes Ave.) College students and the public alike have long flocked to Hemmingways for drinks, dinner and more. Apps on the menu include wings, pierogies, poutine and cardiac stix – that’s deep-fried provolone sticks tossed with buffalo sauce and topped with cheddar jack cheese and bacon, and of course, a side of bleu cheese dressing. Salads, entrees and even an entire section dedicated to various grilled cheese sandwiches round out the menu. Choose from 44 beers on tap and check out all of the old bottle caps in the bar.


JoAnne Klimovich Harrop | Tribune-Review

The Porch Schenley in Oakland The Porch Schenley in Oakland

The Porch at Schenley: (221 Schenley Drive) College students and visitors frequent this popular dining spot in the heart of Oakland. Pizzas, bar bees, salads, rotisserie-grilled meats, drinks and open air, outdoor seating. The Porch features gigantic, windows, quirky odd light fixtures and a large wood-fired door.

Union Grill: (413 S. Craig St.) Comfort food like the 5-hour pot of roast and mashed potatoes, burgers, sandwiches and waffle cut fries along with aa friendly bar staff greet visitors at this Craig Street mainstay.

Spice Island Tea House: (253 Atwood St.): Tasty Thai food, stir fries and curries at this beloved spot off Forbes Avenue.


Caliban Book Shop: (410 S. Craig St.) The store for the bibliophile, Caliban is more than just an independent used book store. It also features rare finds, curated book lists and records and CDs, all at prices that they say are below the typical online seller.

Maggie & Stella’s Cards & Gifts: (3925 Fifth Ave.) Located on the ground floor of Pitt’s McCormick Hall, this cute shop carries exactly what its name implies. They carry bath and body items, jewelry and accessories, home decor and more.

The Pitt Shop: (3939 Forbes Ave.) Looking for Pitt Panthers gear? Look no further. This is your go-to place for all things Pitt-themed – apparel, accessories and more.

Phantom of the Attic: Phantom Comics (411 S. Craig St.) and Phantom Games (406 S. Craig St.) are havens for gamers and comic fans.

Interesting places

Panther Hollow: One of Pittsburgh’s first Italian neighborhoods, Panther Hollow sits in a valley below Joncaire Street and the Phipps Conservatory and Botanical Gardens. It’s within the boundaries of Schenley Park, and Panther Hollow Lake is a serene spot that provides respite from the bustling neighborhood.

Schenley Farms Historic District: Located in North Oakland, pristine homes full of character sit on about 170 acres that used to belong to Mary Schenley. The Schenley Farms “model city” was designed in 1905 by FF Nicola to “complement the elegant classical monuments and buildings being erected in Oakland,” according to schenleyfarms.org. Today, because it is a city, state and national historic district, homeowners must adhere to zoning and preservation requirements. Fun fact: It was the first neighborhood in the United States to bury its utility lines underground.

Cinema in the Park at Flagstaff Hill every summer: For high school kids, it’s the place to be seen. For families, it’s the place where movies can be seen. Outside.

Schenley Plaza: The opposite of that famed Joni Mitchell song, a parking lot was razed and a park put in its place. Schenley Plaza sits between the Hillman Library and the Carnegie Library of Pittsburgh’s main branch and boasts the PNC Carousel, The Porch at the Schenley restaurant, the Mary Schenley Memorial Fountain and the green space galore.

Phipps Conservatory and Botanical Gardens: (1 Schenley Drive) Mick Jagger stopped here and smelled the roses, or some flowers, at this Pittsburgh destination during his fall 2021 visit to the city for a concert. Catch the orchid and bonsai show through March 6.

Stephen Foster Memorial Museum 🙁4301 Forbes Ave.) The 12-sided Gothic structure is abundant with stained-glass windows, all illustrating “the father of American music’s” songs. It’s currently open by appointment only.

The Log Cabin: To celebrate the University of Pittsburgh’s bicentennial in 1987, this log cabin was reconstructed to symbolize Pitt’s beginnings as a frontier academy of higher learning.

Hillman Library: (3960 Forbes Ave.) Pitt’s main library is enormous, containing around 1.5 million volumes, more than 200 computers, study nooks and more. It is currently under renovation – the first and second floors closed last August, and will remain so for a total of 18 months. The third and fourth floors have already been revamped.


• Things to do in Shadyside
• Things to do in Lawrenceville

Leave a Comment

Your email address will not be published.