Things to do in Pittsburgh: 24 Hours in the Steel City

When you think of Pittsburgh you most likely think of the Penguins or the Steelers, not history and art. Pittsburgh is known more for its sports than anything else. As a born and raised Pennsylvanian, I have never really ventured to the other side of my state to explore what Pittsburgh had to offer. Recently, I had a chance to explore Pittsburgh before my younger brother’s college graduation at a nearby college. From Fred Rogers to art, this Pittsburgh itinerary has it all.

Phipps Conservatory – $20 for Non-members

Anyone familiar with Eastern PA has heard of Longwood Gardens, but if you’re from Western PA you’ve definitely heard of the Phipps Conservatory. The conservatory is housed in an oversized Victorian greenhouse with several rooms for various flora, including a humid Cuban inspired space. In terms of COVID friendly protocol, the Conservatory is done through timed entries with walking guides throughout. In the future, I hope they keep these pieces of the protocol as they allow for a less stressful visit.

The Conservatory is currently doing a troll-inspired exhibit with different examples of mythical trolls dispersed throughout that sing, make sounds, and even tell riddles! This is the perfect place to visit regardless of if you go alone or bring the whole family. What is unique about the space is that it feels completely immersive, the attention to detail in many of the rooms is impressive and you can easily be transported to a different time and space.

The Conservatory is currently doing timed-entry tickets with a few closed exhibits. Advanced tickets are recommended.

Randyland – Free

As the saying goes, “one man’s trash is another man’s treasure”. Randyland takes that phrase and runs with it. Randyland is a collection of found objects that have been painted and manipulated by the whimsical Randy (no last name). It feels both familiar and strange to visitors who describe it as something from a long-forgotten dream. The bright, vibrant colors and whimsy of his design create an environment that is both timeless and nostalgic for visitors.

I was only able to explore the outdoor garden but it was more than enough. When I arrived on-site, it felt as if I stepped into a place of magic and imagination. As you walk through the gates of Randyland that feeling of nostalgia hits you in a wave. To your left is an unmanned gift shop that operates on the honor system, something that not many places do, however it just seems right. You can Venmo the artist for whatever you purchase in his gift shop. The garden extends back from the gates and to the right with pathways between different zones. Straight ahead is a mirror wall and a small sitting area. To the right is a sitting area with a zone for children where they can play with toys provided by Randy himself. He does ask that you clean up after your children. The back wall is covered in signs with “hello” in different languages adorned with flags.

Randyland is located a few blocks from another avant-garde art installation, the Mattress Factory. Both sites can be visited with very little travel time between the two. Due to COVID, this Pittsburgh treasure only visitors to see the outdoor garden, which is a chaotic oasis in the middle of a bustling city. Randyland is a must-add to your Pittsburgh itinerary.

Please note though that the floor is sand so it may not be level and not ideal for some wheelchair users or those with mobility issues.

The Mattress Factory – $20 for Non-members

The Mattress Factory is somewhat of a collage of separate pieces that work together to create works of art that evoke strong emotions. Split into three buildings and a garden, the Mattress Factory is what happens when contemporary, immersive art and installations combine to create something otherworldly. When you arrive at your scheduled time the front desk suggests that you start in the Maher building then move to

The first of three museums, the Maher installation “A Second Home” evokes almost an uneasy, dreamlike state. Where familiar images and sounds become almost surreal and detached. As you progress the feeling of unease gets stronger and the images more disjointed. When I spoke with several people visiting at the same time they described it as “familiar but fragmented”. I would not suggest this for those with mobility aids as it does have uneven surfaces.

The second museum, the Annex, is much more varied than the first. The Annex is a mix of both permanent installations and current exhibits. Currently, the first floor is home to an exhibit that rivals even the most diligent of entomologist’s collections. You might think that this exhibit would make someone squeamish but it was interesting to look through the display cases and examine the designs on the wall. The second and third floors have a mixture of permanent installations and current exhibitions.

The main building of Mattress Factory is a mix of permanent and current exhibitions. Employees suggest starting at the 6th floor and moving down through the exhibits. Some exhibits are very dark or have flashes of light so if you are light-sensitive, pay attention to the warnings on the plaques. The Repetitive Vision installation by Yayoi Kusama is probably my favorite in the main building.

Timed entries required. Parking available in front of the main building. Some exhibits have adult themes. This is a must do on your Pittsburgh itinerary.

Duquesne Incline – $5 for the ride $5 for Parking

Arguably one of the most recognizable features of the Pittsburgh landscape, the Duquesne Incline overlooks the 3 rivers of Pittsburgh proper. Here you can ride a cable car up a hillside for stunning views of the rivers and Pittsburgh. Located across from the Fred Rogers statue, the Duquesne Incline has been operational for over 144 years!
There are a few things to consider when riding the Incline. First, it is cash only and the only pay station is in the lower station. It is a $5 round trip and parking at the bottom of the incline is $5. The lower station is not wheelchair accessible, but the upper station is, however you will have to pay when you get to the bottom station. At the upper station there is a small museum that explains the history of the incline with an insider view of the hoists that pull the cars up the incline.

If you want to experience a piece of Pittsburgh history with a view add this to your Pittsburgh itinerary.

Fred Rogers Statue – Free

If you grew up in the United States anywhere between 1968 to 2005 you probably grew up watching Mister Roger’s Neighborhood on PBS. Mister Roger’s Neighborhood was a show that taught children about things like loss, racism, and social-emotional learning using puppets. Shot and produced in Pittsburgh, the show inspired thousands of children and several generations. The Mister Rogers Memorial sits overlooking the 3 rivers on Pittsburgh’s shoreline. Here you can visit a statue of the man who impacted so many lives through his message of acceptance.

The memorial is open to the public and is free to visit. Parking is available nearby. The Memorial sits along the river walk.

The Cathedral of Learning and Schenley Plaza – Free

The Cathedral of Learning is the main class building for Pittsburgh University. Pitt sits on a sprawling campus, however, the Cathedral is one of the tallest academic buildings in existence. It is the tallest Gothic architecture structure in the western hemisphere and towers over the city. Non-students cannot go inside, however, it is a marvel of human engineering.

The surrounding area is also lovely to walk around with the nearby Schenley Plaza where you can eat, drink, and play within view of the Cathy. Here a wide variety of restaurants and small food stalls offer a wide range of foods from around the world. Schenley Plaza is also home to kid-friendly attractions such as a carousel and a wide-open grass location beyond the food stalls.

If you want to read more about my adventures check out some of my previous posts on Asia or Canada!