Pittsburgh in One Day: A 24-Hour Trip Itinerary
Can you see Pittsburgh in a day?
About a four-hour drive from Washington DC, I set out to see what I could experience in Pittsburgh in one day. I had never been to the city, instead focusing my Pennsylvania travel on Philadelphia, the Poconos, and a couple of trips to Amish country.
Quirky art at Randyland
Randyland is one of the most unique places to visit in Pittsburgh. Randyland is a public, outdoor art installation/museum started and owned by Randy Gilson. His home and large backyard area is decorated with colorful paint and quirky found objects. Think mannequins, old children’s toys, and retro yard sale finds. It is constantly changing as Randy adds and changes elements all the time.
Entry is free and the museum is open most every day between 10 am and 5 pm. It’s a quick walk-through so it’s perfect for when you are short on time. You might see Randy while you’re there, painting or assembling something. He’s very nice and open to a chat. He definitely has an inspiring story to tell, coming from poverty and homelessness to community activism and guerilla gardening in the city.






Art and history museums
If you are a fan of museums and historic centers, Pittsburgh is home to the Andy Warhol Museum, the Heinz History Center, Phipps Conservatory and Botanical Gardens, Carnegie Museum of Art and Natural History, and the Frick Museum and Gardens, among other smaller museums. The August Wilson African American Cultural Center is also a great place to see changing exhibitions, performances, and participate in arts events.
Shop and dine at the Strip District Terminal

The Terminal in the Strip District is a large market with tons of restaurants, shops, indoor and outdoor seating, office space, and events. It’s a great place to eat and shop when you want multiple options in one place. They have a wide range of vendors including a winery, nail spa, fitness studios, mini golf, a hoagie shop, Asian food hall, and big chains like Chipotle and Sephora.
Check their events calendar to see what’s going on at the moment. They host events like yoga classes, game day rallies, and a beer and chess club.
City views from the Duquesne Incline
Riding the cable car up the Duquesne Incline is the best way to get a vast Pittsburgh city view. The incline opened in 1877 and was restored in the 1960s with the original wooden cable cars. For adults, cash-only fares are $2.50 one-way or $5 for a round trip.


Dinner with a view
After riding the tram up the Duquesne Incline, we got dinner at seafood restaurant, Monterey Bay Fish Grotto. The view is definitely a focal point with a glass elevator to bring you to the restaurant and floor-to-ceiling windows all around. For the same sweeping view, you can also dine at other restaurants on Grandview Avenue in Mount Washington like Grand Concourse.
Detour to Frank Lloyd Wright’s Fallingwater
We carved out some time specifically to visit Fallingwater in Mill Run, PA, about an hour’s drive southwest of Pittsburgh. Fallingwater is a house designed by the architect Frank Lloyd Wright in 1935. It’s an example of his organic architecture philosophy, where art and nature exist in harmony. The house is built over a waterfall and parts of it blend into the surrounding rock.
Guided tours of the outside and inside of the house are available, as well as plenty of space to explore on your own. One thing you must do is walk to the lookout spot to see the most well-known vantage point of the house and the waterfall. They also have a gift shop with a lot of great souvenirs- I bought a set of tumbler glasses and blank greeting cards with Frank Lloyd Wright-style designs.




A grounds pass, which does not include the interior of the house, costs $18. Guided tours that include the interior and exterior cost $42 and there are multiple other tour options.
Is Pittsburgh worth a day trip?
Yes! Pittsburgh has plenty to do, but it’s not so big that it’s overwhelming. If you want to experience the highlights of this growing and changing rust belt city, you can’t go wrong with this Pittsburgh in one day itinerary.
If you liked this, check these out:
How to Explore Philadelphia in One Day
Fall Foliage and Halloween Spirit in the Poconos, Pennsylvania
How to Spend a Day in Pennsylvania Amish Country
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