I visited Pittsburgh a few times as a child, usually for field trips to the Carnegie Museums, and I remember thinking that it was a magnificent city. Admittedly, I was not really familiar with it at all, but the magic of going through the Fort Pitt Tunnel and having the city materialize always felt a little magical. Growing up in West Virginia, the “big city” I was familiar with was Charleston, which is not all that big of a city. I once heard Pittsburgh described as “the Paris of Appalachia,” and it’s a sentiment that has never left my mind because it feels like an apt description for this gem of a city that’s tucked into these mountains.
Living in Morgantown, WV now, I’m only about an hour away from Pittsburgh, so I’ve been fortunate to visit it much more often than I did as a child. And, to me, it still holds some of that magic I first discovered there. Pittsburgh is easily one of my favorite destinations for a day trip or weekend trip out of Morgantown, and while I have a lot more to explore in the city, I’m excited to share a few of my favorite places. I have a lot to say about Pittsburgh and what to do there, so I’ll be making a few different posts on the city. This three-day itinerary is a bit of an introduction and overview of what you could do on a regular weekend, but keep an eye out for more Pittsburgh posts soon!
Day 1: North Shore
For this itinerary, we are assuming that you arrive on a Friday afternoon/evening to visit the city, so Day 1 is a bit limited. For me, a trip to Pittsburgh always involves driving through the Fort Pitt Tunnel. Sure you can get into the city another way, and yes, there can be traffic going into the city, but the view of Pittsburgh appearing when you exit the tunnel can’t be beat!
Once you’ve made your way into the city, I recommend checking in at my personal favorite bed and breakfast in Pittsburgh: The Inn on the Mexican War Streets. This is a gorgeous, historical building that feels fancy but is actually affordable, and it’s close to a lot of great sites on the North Shore!
After settling in, it’s time to get dinner. My top recommendation is Legends Eatery, which was actually recommended to us by one of the owners of The Inn on the Mexican War Streets. It’s a little pricey, but not too expensive, and the food is worth every penny! As a bonus, it’s about a ten-minute walk from The Inn, so you won’t need to find parking on the street. Other dinner options in the area include Pauline’s Caribbean Soul Food Cuisine (primarily carry out with only a couple tables). I’ve also heard good things about Max’s Allegheny Tavern, but this one is still on our list to try (I’ll update the post once I’ve been there).
Following dinner, I suggest taking a walk to explore Randyland, which is a unique Pittsburgh experience. Randyland is essentially a massive art installation created by the owner, Randy Gilson, who moved to the neighborhood in 1982. A colorful, happy space, Randyland is internationally known and has been influential to Pittsburgh’s rejuvenation over the past few decades. Randyland is free to visit though donations are accepted, and you can spend as much time as you like exploring. You may even meet Randy himself while you’re there!
Pittsburgh has lots of bars if you’d like to keep the evening going; in particular, the Monterey Pub is located close to The Inn and has the fun energy of a classic Irish Pub. If you’d prefer a quiet night in, The Inn on the Mexican War Streets has a few different common areas where you can spend some time reading or talking and maybe getting to know some of your fellow guests. These common areas were one of our favorite parts about staying here, and another reason why we love this inn!
Day 2: See the Sights
This is your main day for exploring what Pittsburgh has to offer. Pittsburgh has several top tier museums, and it would be impossible to see them all in one weekend. I’m hoping to write a more in-depth post discussing the different museums, but here are a few top recommendations:
For Art Lovers: The Warhol
The Andy Warhol Museum (or just, The Warhol) is home to the world’s largest collection of Andy Warhol art and archives. The famous artist was born in Pittsburgh, and the city is still very fond of him. Warhol was an experimentalist who did a lot more than just Campbell’s Soup Cans! Art lovers will not want to miss this museum, and I recommend doing a guided tour if you are able to!
For Those Who Love to Learn: The Carnegie Museum of Art and Natural History
Andrew Carnegie is a famous patron of Pittsburgh, and there are several museums that are part of this legacy. The Carnegie Museums of Art and Natural History is one large building with everything from dinosaurs to Van Gogh and even a small exhibit about Pittsburgh and the Carnegie Museums. You can spend hours getting lost (literally) in this museum, and it has so much to offer that everyone can find something interesting!
For Families: The Children’s Museum of Pittsburgh
If you’re visiting with children, the Children’s Museum of Pittsburgh is an incredible place to spend a day. This is one of the foremost children’s museums in the county with activities for toddlers to teenagers (and a lot of fun for adults too)! This is also a great option if you end up needing a rainy-day activity in the city since it is all indoors. One of the most exciting things for me in visiting this museum was seeing the original puppets from Mr. Roger’s Neighborhood (Mr. Rogers also lived and worked in Pittsburgh).
The Duquesne Incline
Following a morning (or morning and early afternoon) at the museum of your choice, I recommend grabbing a quick lunch then heading to the Duquesne Incline. While not something I do on every single trip to Pittsburgh, it’s something that everyone should do at least once. If you only have a couple days in the city, this has to be on your list. Depending on the season that you visit, the line for the incline may be a bit long, but it usually moves quickly. For a few dollars, you can ride a funicular car up the side of the mountain to Pittsburgh’s Washington Heights neighborhood for incredible views over the city. Take your time enjoying the view and walking around the neighborhood before you head back down to the main part of the city.
The Strip District
With the rest of your day, I suggest heading to The Strip District. There are a lot of amazing shops here, but the specialty is food. I have friends who periodically drive from Morgantown to the Strip District specifically to stock up on certain cheeses. When visiting this area, park on Smallman St. and take some time to walk around. Explore a few specialty grocery stores or Love, Pittsburgh for some souvenirs. And hit up my favorite store in the area: Posman Books!
Dinner in the Strip District can be a challenging decision with so many incredible restaurants, but my favorite is Roland’s Seafood Grill. Wherever you go though, you’re sure to find amazing food in this neighborhood.
For your second evening in Pittsburgh, if you still have energy, I suggest seeing a show or finding some live music. On a Saturday night in Pittsburgh, you’ll have lots of options and can find something amazing in any neighborhood. My most iconic Saturday night in Pittsburgh was undoubtedly seeing The Eras Tour, but that’s not an every weekend event. My top recommendation that I have yet to see is a newcomer to Pittsburgh – Candlelight Concerts. I saw one of these performances in Cleveland, and it was a gorgeous way to spend an evening. Whatever you choose for the evening, you can expect to be entertained by the arts in Pittsburgh!
Day 3: Squirrel Hill & Point State Park
For your last day in Pittsburgh, it’s time to hit a few smaller sites. If you have time, I of course suggest seeing another museum, but if you’re leaving the city in the afternoon, you have just enough time for a couple of smaller activities.
The Inn on the Mexican War Streets provides breakfast (another plug for them), but for a sweet, decadent brunch, I have to recommend Waffallonia in Squirrel Hill. This is an adorable little restaurant serving Belgian waffles, which you can top with fruit, Nutella, or even ice cream – though I’d save that last one for a dessert later in the day.
While you’re in the area, you may as well stop at Amazing Books and Records to support another small business. (Bonus: If you stay the night in Squirrel Hill or stop by on a Saturday evening, you can enjoy a free beer while you browse the store!) We love visiting Squirrel Hill and walking around all the little shops in this neighborhood, so feel free to spend a bit of time here enjoying the city life.
For a final stop in the city, you’ll head back downtown to see Point State Park and the fountain here. This is a lovely waterfront area where you can relax a bit and watch people and boats go by. Be warned, parking may be a bit difficult or expensive to find nearby, but this park is a lovely place to spend a bit of time before you leave the city.
Final Thoughts
Pittsburgh is one of my favorite places to visit, and although this post mentioned several of my favorite spots, I also left a lot out! I hope to share more exciting pieces of Pittsburgh soon and encourage everyone to spend a bit of time in the “Paris of Appalachia!”
Wonderlust Wanderings 