Breeze Airlines has made it easy and affordable to take a random weekend getaway to Pittsburgh from where we live in Raleigh. Friends of ours did it recently and recommended it so we thought we’d give it a try. Why not? And it turns out that Pittsburgh possesses the unique charm of a city perpetually teetering on the edge of revival.
Pittsburgh boasts a skyline of abandoned steel mills and soot-blackened skyscrapers under the ever-present threat of rain. But on a clear day, the view from atop Mount Washington can be quite breathtaking, though you might still find yourself wincing at the sight of the steel mills below. Yellow bridges, as intricate as metal cobwebs, span the three (yes three) rivers snaking through the heart of the city.
The people of Pittsburgh represent a particular breed of humanity, presumably forged in the fires of industry and hardened by miserable weather. They almost all sport black, bleach-blond, or technicolor hair, and a surprising number choose to wear fursuits. One might expect them to be loud and abrasive, everready for a fight, but they possess a surprising steely resolve and quiet wit. Their clothes are practical and unpretentious, often showcasing the logos of their favorite sports teams – a testament to their unwavering faith in the black and yellow.
So, dear reader, if you find yourself drawn to Pittsburgh, be warned. It is a place where misfortune can lurk around every corner, disguised as a surprise thunderstorm or a particularly steep incline. But for those who seek adventure, Pittsburgh might just be the place for you. Just be sure to pack a good raincoat, an extra pair of dry walking shoes, and a healthy dose of cynicism.
I’m sharing things we did as well as things that sound fun and would be worth checking out on my next weekend in Pittsburgh.
- How to Get Around in Pittsburgh, PA
- What to See and Do in Pittsburgh, PA
- Where to Stay in Pittsburgh, PA
- Where to Eat and Drink in Pittsburgh, PA
- Itinerary for a Weekend in Pittsburgh, PA
Don’t miss out on this! This article is also featured on GPSmyCity. To download this article for offline reading or create a self-guided walking tour to visit the attractions highlighted in this article, go to Walking Tours and Articles in Pittsburgh.
How to Get Around in Pittsburgh, PA
Walking is a good option given that you can walk from one end of Downtown Pittsburgh to the other in 25 minutes.
- Take advantage of the POGOH bike share system. They have both regular and e-assist bikes.
- There are currently no scooter share programs in Pittsburgh, but keep an eye out for a possible reintroduction in the future.
- Ride Pittsburgh Regional Transit (PRT) busses, light rail trains, and Inclines (aka funiculars). There is a light rail free fare zone Downtown between the First Side and North Shore stops. Use Google Maps or the Transit App to check routes and fares.
- Lyft and Uber ride share and zTrip taxis are also available.
What to See and Do in Pittsburgh, PA
Unveil Pittsburgh’s rich past at Point State Park, a captivating historical oasis at the convergence of the city’s famed “golden triangle.” Immerse yourself in the stories of the French and Indian War, the American Revolution, and Pittsburgh’s early rise at the Fort Pitt Museum. This 12,000 square foot treasure trove stands upon the very foundation of historic Fort Pitt, once North America’s most formidable fortification. The park further boasts the Fort Pitt Block House, a testament to Pittsburgh’s enduring legacy, predating even the American Revolution itself. To be honest, we spent very little time at Point State Park because they were going wild blasting a cannon every few minutes, presumably as part of their Fourth of July celebrations – not exactly my idea of a good time.
Take a ride on Pittsburgh’s historic Inclines (Duquesne & Monongahela) built in the late 1800s. They zip up Mt. Washington (previously known as Coal Hill) every 5-10 minutes for stunning city views. The restored Duquesne Incline (1877) has charming wooden cable cars, and you can see its inner workings!
Soak in a breathtaking panorama from the Grandview Overlook, perched atop Mount Washington. Gaze upon the Allegheny and Monongahela Rivers, and watch the city skyline unfurl before you. Once a quiet spot with a view, it’s now a charming park, perfect for a relaxing escape.
Explore Pittsburgh’s Strip District. Once a hub for heavy industry and produce markets, it’s transformed into a vibrant neighborhood brimming with flavor. Abandoned mills stand proudly beside bustling international markets, while trendy restaurants share the sidewalk with delis stacked with local treats. Don’t miss Grandpa Joe’s Candy Shop – I am generally disappointed in candy stores, but this one is legit. And they have unusual games for sale too!
Nestled in Schenley Park’s northwest corner, Phipps Conservatory stuns visitors with its impressive steel-and-glass architecture and meticulously designed (and themed) gardens. The theme when we visited was “Under the Sea” – try to find the lobster hiding in every garden. Regular admission is $21.95.
Built in the 1920s and soaring over Pittsburgh, the University of Pittsburgh’s Cathedral of Learning isn’t just a building, it’s a landmark. This 42-story Gothic masterpiece houses classrooms, a theater, and even a food court! Explore the incredible Nationality and Heritage Rooms – 31 unique classrooms celebrating global cultures. Self-guided audio tours are available on weekdays during school term and 30 and 90 minute guided tours are available in the summer and outside class hours. Sign up for a tour online starting a $5 for adults.
Step into the enigmatic mansion of Charles Brown! The Bayernhof Museum is a grand, preserved house that holds a secret symphony within its walls. Discover hidden doors and passageways, all leading to a remarkable collection – dozens upon dozens of automated instruments, ready to fill the air with unexpected melodies. You need to call ahead to schedule a tour, which of course I failed to do.
Since 1977, Mattress Factory stuns with incredibly unexpected art. Explore wild installations, from dark sensory rooms to gravity-bending spaces. Expect thought-provoking immersive art. Regular admission is $22.
Pop art legend Andy Warhol gets his due at The Andy Warhol Museum. Dive into the world’s largest collection of his work, from early sketches to a recreated Factory experience. Get hands-on, see his video works, and grab pop art souvenirs at The Warhol Store. Regular admission is $25.
Randyland is a riot of color created by local artist Randy. Forget boring, this is a color explosion! Imagine a giant yellow house, murals that reach the sky, and a quirky army of painted garden gnomes. Discarded furniture reborn in rainbows shares space with vintage treasures. It’s a celebration of oddness and color, a must-see! It’s free to visit and doesn’t have to take much time so try to fit it in.
Bicycle Heaven is the world’s biggest bike shop and also a free museum showcasing over 4,000 vintage bicycles from across the globe. Explore cycling history, then browse the latest rides – the perfect place to find your new two-wheeled companion (and maybe a U-lock to keep it safe!). It’s free to visit but we didn’t manage to fit it in on this trip.
Visit any number of other Pittsburgh museums such as the Senator John Heinz History Center (for all sorts of Western Pennsylvania history), Carnegie Museum of Natural History (for a real Tyrannosaurus rex skeleton), or Carnegie Museum of Art (for contemporary art).
Board a Gateway Clipper for a sightseeing, dinner, on ghost cruise through the waters of the three rivers area, providing spectacular views, meals and libations for those who want to see the city from the water. We didn’t do this, largely because the weather was so unpredictable.
Journey back in time with Rivers of Steel‘s captivating tour of Pittsburgh’s industrial heart: the Carrie Blast Furnaces National Landmark. This once-mighty site, a remnant of U.S. Steel’s Homestead Works, sheds light on a defining era of American manufacturing. The two hour tour delves into the fascinating story of steel production, the lives of the steelworkers who powered the industry, and the vast network that supplied the building blocks of 20th-century America. The tour is $25 for adults and you should get your tickets online ahead of time. This is a good ways away from Downtown Pittsburgh so it’s on my list for our next weekend trip.
Where to Stay in Pittsburgh, PA
There seem to tons of good accomodation options in Pittsburgh, though rates were through the roof for the weekend that I was booking so plan ahead!
We stayed at the Maverick by Kasa. In a repurposed YMCA, it had a funky vibe, was affordable, and was near a few good restaurants and grocery stores. That said, it was not particularly close to any attractions so did require us to use a rideshare or bikeshare to get downtown.
Renaissance Pittsburgh Hotel – luxury hotel in a historic building with comfortable rooms and a prime location.
Fairmont Pittsburgh – sophisticated hotel in a super convenient location for a weekend trip.
Kimpton Hotel Monaco Pittsburgh – quirky and inviting luxury boutique hotel. It’s in a super convenient location, but doesn’t have all of the bells and whistles you might expect.
Where to Eat and Drink in Pittsburgh, PA
Coffee and breakfast:
- Be prepared to set your alarm for Better-Maid Donut Co.‘s legendary donuts! This beloved shop sells out fast, especially their coveted donut holes, which vanish in a flash. Lines form as early as the 6 am weekday opening (7 am on weekends), and the party ends when the donuts are gone – sometimes within two glorious hours. I’m amazed that we never made it here over a whole weekend in Pittsburgh given how much my husband loves donuts.
- Pamela’s is a popular spot for breakfast. There are six locations around the city, but the one in the Strip District is the most famous. It’s so famous that President Obama even ate there in 2008! If you’re looking for a hearty breakfast, Pamela’s is the place to go. I’ve been told to try the Morning After.
Lunch:
- Ephesus serves up unique, Mediterranean-inspired pizzas. Craving adventure? Try their gourmet pies featuring lamb kebabs, Moroccan chicken with dates, or even Turkish pepperoni. Still a traditionalist? No worries, they have classic options too. Ephesus goes beyond pizza, offering a full spread of Mediterranean delights: baba ghanoush, grape leaves, falafel, gyros, and even wings.
- Huszar is a charming restaurant that transports you straight to Hungary with its menu of classic dishes. Savor rich goulash, tender chicken paprikash in a creamy paprika sauce with dumplings, and crispy langos. This is in a slightly weird location but sounds so good!
- Cilantro & Ajo offers a delicious taste of Venezuelan street food. They’ve got all the classics: handmade arepas, savory empanadas, and sweet cachapas. Most of their food is friendly for those with gluten sensitivities, and also very affordable.
- Peppi’s has been a Pittsburgh favorite since 1983. They’re famous for their steak, chicken, and Italian subs, but their real claim to fame is the Pittsburgh-style salad. Unlike traditional salads, this one ditches the croutons and tops it with fresh-cut fries! Peppi’s version, called the “now famous” steak salad, is a perfect example: it’s loaded with juicy steak, crispy fries, and melty provolone cheese. This was surprisingly good, and a veggie-heavy meal is always appreciated.
- No Pittsburgh visit is complete without pierogies! S&D Polish Deli is a haven for all things Polish (and delicious). This market isn’t fancy, but it delivers fresh meats, sausages, and pastries alongside their true star – pierogies. Sample their delightful pockets filled with classics like sauerkraut and mushroom, or explore sweet options like cherry or blueberry. Craving something comforting? Don’t miss their haluszki, a Pittsburgh staple featuring soft egg noodles with sweet cabbage, onions, and a buttery finish. So yummy.
- Täkō, a playful mashup of “tako” (Japanese for octopus) and “taco,” brings the bold flavors of Southern California to Pittsburgh. Imagine a vibrant surf shack serving up some of the city’s most delicious Mexican fare. I’m sad we weren’t able to get here to try the papas bravas.
- Pittsburgh’s blue-collar roots run deep, and Primanti Bros. is a delicious testament to that. Sure, they offer wings, pizza, and cheese fries, but the real stars are the “almost famous” sandwiches. Here, they take the classic sandwich and turn it up to eleven. Imagine cold cuts, coleslaw, and a pile of fries all nestled between hearty Italian bread. Pure genius, perfect for a late-night bite after a night on the town. Pro tip: one sandwich should be enough for at least two people.
Dinner:
- Perched atop Mount Washington, Monterey Bay Fish Grotto offers unparalleled panoramic views of Pittsburgh’s twinkling skyline and the three rivers below. The romantic ambiance with soft music and dim lighting sets the stage for a truly unforgettable experience. Indulge in their award-winning fresh seafood, succulent cuts of beef, and decadent sides like truffle fries. Don’t miss their signature MB Mac n’ Cheese, overflowing with snow crab and Mexican paradise shrimp. We didn’t make it here but it will definitely be on our next itinerary!
- Immerse yourself in the soulful sounds of jazz at Con Alma, a restaurant and bar that sits in Pittsburgh’s Cultural District. The chef curates a menu of Latin-inspired creations like albacore xnipec with chips, bacalaitos, and lechon asado, alongside global favorites like dan dan mian and Korean fried chicken. This Esquire-recognized hotspot also boasts an impressive cocktail program (no joke), complementing the vibrant atmosphere. Live jazz performances feature Pittsburgh legends.
- Driftwood Oven isn’t just about delicious pies, it’s about conscious cuisine. The chef champions ethical sourcing, using only the finest ingredients. Their sourdough crust starts with 100% organic whole grains, while fresh meats come from local Goodness Grows Farm. Even the mozzarella, ricotta, and provolone boast a pedigree – all grass-fed cattle milk from Caputo Brothers Creamery. The result? Amazing Roman square pizzas. Sample a house favorite like the bianca or pepperoni, or get adventurous with their specialty toppings – peach and corn were featured when we visited.
Desserts:
- Step into Prantl’s Bakery and you might just experience the “best cake in America,” according to HuffPost and countless fans. Their signature burnt almond torte is legendary: a melt-in-your-mouth custard-filled square cake topped with light buttercream and candied toasted almonds.
Drinks:
- Nestled on the slopes of Mount Washington is The Summit, a haven for casual afternoons and cozy evenings. This bar offers elevated pub fare (think tasty hotdogs) alongside creative cocktails.
- The Warren Bar & Burrow is a laid-back spot in the cultural district offers pan-Asian shared plates, bowls, and sandwiches alongside creative cocktails. The speakeasy atmosphere, made-to-order sushi have made it a popular hangout. – We didn’t make it here this time.
- In the heart of the Cultural District, Bridges & Bourbon is your spot for show-stopping cocktails.
- Church Brew Works, as the name suggests, inhabits a deconsecrated church. Step inside and you’ll find the brewing equipment at the altar, pews replaced with comfy dining tables, and the original stained glass windows gleaming. They do serve food but with over a dozen styles on tap, from Dunkelweizen to Baltic Porter, there might be a brew to please every palate.
- Soju is a funky casual Korean-ish restaurant with fun food and creative cocktail. Get the Waikiki Spam Jam and Korean Poutine.
Itinerary for a Weekend in Pittsburgh, PA
We had two and a half days in Pittsburgh and I think that was perfect. On the other hand, I could easily fill two more days, but I’d rather do that on a second trip. That said, I’m not going to spell out a detailed itinerary for you because you may want to do slightly different things than we did, but hit me up if you want help coming up with your own personalized itinerary. Here’s my Google Map that you can use to start planning your own adventure in Pittsburgh, Pennsylvania.
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