I first visited Pittsburgh for four days in 2021 on a cross country train trip with my husband. During the COVID lockdowns, I spent a year planning the train trip as my form of stress relief (more on that later). Out of the 11 cities we visited over 30 days, including Chicago, DC, and NYC (which we ended up moving to), it was our surprise favorite! We remember it so fondly that whenever our NYC rent increases or we want a change of pace, Pittsburgh is always one of the places we consider moving to.
My second visit happened during an 18 hour layover this fall as a flight attendant. It reminded me of all the good memories as I visited old spots and new. The city and the people are a little rough around the edges, but I have always been treated nicely. You can see in the buildings downtown the impact of the steel industry when that business was booming. And still to this day, foundations bring some of the best art and culture to this little corner of the country.Here are some of my top spots (and a few places I still want to try on my next visit)
Stayed here on a layover and loved it. The happy hour is two drinks per person and the breakfast is included (ask for it to go if you have an early morning) plus perfect location!
Pittsburgh is the City of Bridges, with the Allegheny and Monongahela Rivers combining to form the Ohio River. The point is nice to walk around and hosts many food and art fairs during the warmer months. It’s a beautiful walk in the heart of downtown, with a spectacular picture spot!
This museum is hard to describe. It is an interactive and thought-provoking large installation art piece that takes up multiple buildings in the Allegheny Historic District. I am not usually a museum person, but I thoroughly enjoyed myself!
This is just a small part of the University of Pittsburgh, which has so many things to offer from the city. Braden and I have visited many Botanical Gardens and this one was fantastic! Take a look at what seasonal displays they have before visiting as well!
Right around the corner, is the color explosion that is Randyland. Part art museum and part shrine to found art, founded by Randy Gilson in 1995. It is a fun photo op and a great place to get a unique souvenir from Pittsburgh!
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As a bonus, right around the corner from Randyland is Mayfly Market and Deli. I had the best vegan sorbet that the owners make themselves! What a great way to cool down after walking all day.
A must do in Pittsburgh! While there are many other locations, the original in the Strip District has all the charm of Pittsburgh. Make sure to get the classic and bestselling (with fries in the sandwich). The only item they sell more of is beer!
My husband loves sampling the local whiskey wherever we go.. and the whiskey was so good that we carried a bottle of it for the next half of our trip! I still have the bottle as a memento. Very yummy!
You may think that the world’s largest sanctuary for writers in exile may be in a bigger city like NYC or another international powerhouse, but it’s actually in Pittsburgh! They have different artists in residence and other events throughout the week. I love perusing their wide selection of books from authors I may not normally see. Plus, they have a used book section in the back!
This is a fun place to walk around to eat and do some window shopping. It is a mix of converted warehouses from staples like Primanti Brothers and newer places like Wigle distillery!
Originally built to carry cargo and then passengers up to the neighborhood, this unique public transportation is not one to miss. It offers a fantastic view of the downtown and lets you take a step back in history!
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Things I Still Want to Do!
There is still so much to see and do in Pittsburg. Hoping to check more things off my list in a future trip!
Go to a Game for Pittsburgh Steelers or Pirates. Last time I was in town the Pirates were about to play and the mood was electric. From what I know about Pittsburgh, they take their sports teams very seriously!
While he famously did not love his hometown, it was still the place he grew up. I am interested to see the current artist they have on display as well!
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And this blog post has a ton of recommendations that I will be taking under consideration!
Hey it's Hayley !!
Latte enthusiast, used bookstore connoisseur and huge fan of walkable neighborhoods
Having spent at least one day and night in 42 states and counting my specialty is traveling within the USA. I grew up in Southern California, lived for six years in Utah, had a brief stint in Orlando and now on year 2 in New York City.
Want to know the cheapest times and places to fly? My day job is a flight attendant based in NYC!
Trains more your speed? I once spent a month backpacking from Utah to Boston using Amtrak!
Love a long road trip? I have driven across the country three times!
After years of travel planning for my friends and family I thought I would share my resources with the world wide web :) I enjoy planning the trips more then actually leaving for the trips so this is the perfect place for me.
