10 Things to love about Pittsburgh’s Oakland

A few weeks ago as I was walking down Forbes Avenue between Pitt and CMU, I was struck by an amazing scene. It was a beautiful summer day, the sun was out and a light breeze carried cool air along with the bustle of students from all over the world heading to summer classes. The Cathedral of Learning towered over the buildings ahead, its elegant gothic architecture somehow able to complement the classic brick buildings that still line the neighborhood’s business districts. The smell of freshly prepared food was on the air, Frisbees were flying and music could be heard in the distance. It was the perfect reflection of summer in Pittsburgh, past, present and future, and it was all to be had in one place: Oakland.

From my first day of preschool to my last day of graduate school at CMU, Oakland has been the neighborhood where I’ve either lived, been schooled or, most recently, owned a business. It’s a diverse neighborhood that is complex, exciting and defies any sort of neat categorization. Picking my 10 favorite things was not easy, but it sure was fun.

1. Cathedral of Learning

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A good place to start is with Oakland’s most iconic building, the Cathedral of Learning. Home to many classrooms and offices of the University of Pittsburgh, it also happens to be the second tallest educational building in the world, a great place to study and a beautiful building to take in a unique view of the city (head up to the 36th floor to see what I mean). The first floor of the building also happens to be a spitting image of Hogwarts, which is pretty freakin’ awesome.

2. The O

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Technically called Essie’s Original Hot Dog Shop, the O is best known for delicious dogs, enormous quantities of French fries and basically never being closed. Although sometimes given a bad rap, The O is a must-experience Oakland destination. And make sure you bring some friends, because a medium fry comfortably serves four.

3. Dave & Andy’s

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One scoop of birthday cake ice cream + a waffle cone with two M&M’s in the bottom = Dave & Andy’s. Arguably the best ice cream in the city, all of Dave & Andy’s 200 flavors are homemade and delicious. Be warned, though – after you get used to M&M’s in the bottom of the waffle cone, every time you’re finishing up ice cream from another place and there aren’t any in the bottom, it’ll taste like a broken promise.

4. Community

Oakland Pittsburgh Neighborhood

In addition to being home to several vibrant university communities, Oakland also has a very strong local business and resident community. Represented by great organizations like the Oakland Business Improvement District, Oakland Planning and Development Corporation and the Oakland Community Council, all parts of the neighborhood are engaged and working to keep the neighborhood strong.

Photo Credit: Rick Armstrong

5. Innovation Central

Oakland is Pennsylvania’s third largest economic center behind Center City Philly and Downtown Pittsburgh, and one of the reasons for that is the huge amount of innovation coming out the neighborhood’s universities and institutions. Oakland is also home to Revv Oakland, Project Olympus, and Idea Foundry, three startup incubators that support Pittsburgh’s vibrant and growing entrepreneur community.

As of this month, Oakland is also home to the first neighborhood in Pennsylvania with a web mobile app – The Oakland Scene! Check it out to find things to see and do in the neighborhood.

6. Sandwiches

I have a confession to make: I love sandwiches. Thankfully for me, Oakland has the best selection of sandwich awesomeness the city has to offer. In addition to a great Primanti’s location, Oakland also boasts Uncle Sam’s, Fuel & Fuddle, the Pittsburgh Pretzel Sandwich Shop and for something a little different, Eat Unique.

7. Batman

Where does Bane attack Batman? Right next to the columns of Mellon Institute on Fifth Avenue. How awesome is that?

8. Oodles of History and Culture

Between the historic buildings, Carnegie Museums, the Phipps Conservatory and the music and theater performances at Pitt, CMU and the Pittsburgh Playhouse, Oakland offers the widest variety of cultural activities available in Pittsburgh.

9. Schenley Plaza & Park

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Before Schenley Plaza was built, I’d never heard of a parking lot being turned back into paradise. Located between the Cathedral of Learning, Hillman Library, Carnegie Library and Pitt’s Frick Fine Arts Building, Schenley Plaza is in a prime spot for outdoor recreation and relaxation. On Fridays during the summers, WYEP features live music and a little down the way, movies are shown on Flagstaff Hill every Wednesday and Sunday.

10. Public Transportation

After Downtown, there is no other neighborhood in Pittsburgh that is better connected to public transit than Oakland (just ask Pitt and CMU students). It’s one of the reasons that Oakland is active and vibrant year-round, and one of these days we’ll finally get an extension of the T into Oakland (right, Bill Peduto?). 🙂


Oakland really has it all, and this list only scratches the surface. I’d love to hear about what your favorite parts are, and don’t forget to download the Oakland Scene App to connect to great things to see and do in the neighborhood!

Author Profile

Kate Stoltzfus
Kate Stoltzfus
Editor/founder of Yinzpiration.com, CreativeMornings/Pittsburgh host, co-pilot at Propelle, and digital strategist at Plumb media.

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Kate Stoltzfus

Editor/founder of Yinzpiration.com, CreativeMornings/Pittsburgh host, co-pilot at Propelle, and digital strategist at Plumb media.

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