Anyone who has been to Pittsburgh could be easily fooled into thinking this former industrial city was a major metropolitan. Although it’s the second-largest city in the state of Pennsylvania, it sure doesn’t feel like it: it seems much bigger. The city has a lot to offer. It is a mix of world-class museums, fantastic architecture, and acclaimed educational institutions. But with delicious and unfussy food options, it never feels too big for its britches.
A Pittsburgh weekend getaway is urban fun but without all the stresses one normally associates with city travel. The city’s downtown area is relatively compact and accessible for exploring on foot. But if you want to see more of the city, having a car at hand doesn’t hurt. With a car or public transit, you can explore more of this sprawling city with its many distinct neighborhoods.
Pittsburgh also has a small-town feel where people greet you and, no joke, warn you when you’re approaching broken glass on a bridge. Seemingly no matter where you go in the city, it feels personable and welcoming.
Things to Do in Pittsburgh
There’s a little something for everyone in Pittsburgh. For the active and outdoorsy types, there are miles of trails (including lovely riverfront ones) to walk/cycle/run while the rivers are perfect for watersports. And that’s in addition to urban green spaces and squares.
It seems wherever you go in the city — whether the roadways or the waterways — there’s an impressive view. In addition to a variety of historic buildings that will make fans of brick and stonework rejoice, there are bridges. Wherever you turn, there are bridges that you can explore up close. Each one has its own unique details, shapes, structures, and many painted in a bright yellow color.
Monongahela & Duquesne Inclines
For more stunning views, heads to the city’s inclines. Because of the city’s rolling hills and industrial background, there were once about two dozen funicular railways to move workers as well as freight like coal and wood. Today, two of these inclines remain in operation for moving locals and tourists: the Monongahela Incline and the Duquesne Incline. For a $5 roundtrip ticket, you can ride up to the top of the incline to enjoy views over the city and the surrounding area. It’s definitely worth the ride, if only to appreciate the lovingly restored and well-engineered railway.
The number of Pittsburgh museums is just right for any quick trip to the city. Simply focus on the museums of interest to you and you won’t be disappointed. For me, that means the Andy Warhol Museum, the Carnegie Museum of Art, and the Frick Pittsburgh.
First up, the Warhol Museum, celebrating perhaps the city’s most famous artist. And visitors really get to embrace Warhol, from his modest beginnings in Pittsburgh to his glamorous life in NYC. Starting at the top floor of the seven-story building, visitors walk down through the years and many notable works. It’s quite impressive how many works, and how many large-scale works, the museum has on display. That’s in addition to objects, films, and more. The Warhol Museum also hosts additional exhibitions, seamlessly folding them into the permanent collection to compare and contrast for a fresh take on the art.
Across town in the Oakland neighborhood, adjacent to the University of Pittsburgh and Carnegie Mellon University campuses, are The Carnegie Museums of Art and Natural History, which share a building. The Carnegie Museum of Art has a solid collection worth visiting in order to see notable works including Monet’s “Water Lilies,” Edvard Munch’s “Girl under Apple Tree,” and several by Van Gogh. While you’re in Oakland, be sure to go for a walk around the stately university campuses there for some impressive buildings…and at least one unexpected one: a log cabin.
A little farther east and well outside of the limits of downtown is the Frick Pittsburgh, the home of 19th-century industrialist Henry Clay Frick. While you may be familiar with the family’s luxurious home in Manhattan, their Pittsburgh home is just as impressive albeit in quieter surroundings. Visitors to the Frick Pittsburgh can enjoy free admission to the family’s permanent art collection, car and carriage museum, plus a greenhouse and gardens.
Pittsburgh Stript District
The Strip District is a narrow band of land along the Allegheny River just northeast of the downtown that shouldn’t be missed during a Pittsburgh weekend getaway. Today, the neighborhood is full of warehouses converted to cool restaurants, coffee shops, galleries, and stores. But, once upon a time, these were warehouses occupied by Westinghouse and Heinz, due in part to the proximity to the river.
The community here has never completely left. It’s still home to historic churches and some of the city’s favorite restaurants. But, like many similar working neighborhoods across the country, The Strip is being rejuvenated and revitalized. It’s now a blend of new loft apartments and new offices of tech companies along with spots that have been there for decades. It’s also home to the Heinz History Center, a museum dedicated to the city topped with an iconic neon light of a Heinz ketchup bottle.
The vibrant neighborhood is full of new places to explore. Go for a walk along the river and across the Sixteenth Street Bridge for stunning views of the city and the landscape. On the other side, the Heinz factory (now converted to housing) stands proudly. Nearby to the bridge on the Strip-side, stop into the hip De Fer Coffee & Tea and really enjoy the neighborhood with their sidewalk seating.
Take in a Game
Looking for more things to do in Pittsburgh? Whether you prefer baseball, football, or ice hockey, Pittsburgh has a team for you. Taking in a game is a great way to get off your feet, relax for a bit, and have some fun during your Pittsburgh weekend getaway. The stadiums and arenas are all located relatively centrally in the city so it doesn’t take a lot of extra effort to get there. In many cases, you can easily walk from Downtown.
Where to Eat
Kick off your Pittsburgh weekend getaway by treating yourself to Pamela’s Diner. For half a century, the local chain has been feeding the city breakfast and lunch. Consider making the star of your Pittsburgh breakfast their trademark pancakes, which are almost as thin as a crepe but with deliciously crispy edges. But be sure to arrive early as there’s usually a bit of a line to get a table. The diner, with six locations across the city, is friendly and unfussy.
If you didn’t fill up too much at breakfast, then you’ll want to visit Pittsburgh staple Primanti Bros. What started in the 1930s as a cart in the Strip is today a successful chain with more than thirty locations across Pennsylvania and neighboring states. But the sports bar atmosphere is unassuming and inclusive. Oh, and the sandwiches? Primanti Bros. is known for its heaping, hearty sandwiches. Your choice of meat stacked high with tomatoes, homemade coleslaw, French fries, and provolone cheese sandwiched between two slices of Italian bread. While the cold cuts are the most popular choice of meat, I really enjoyed the fried fish.
The city is full of unexpected surprises, including a Hofbräuhaus. You read that right, the world-famous Munich beerhall has several Stateside locations, including this one in the Southside Flats neighborhood. The menu makes a noble attempt at recreating the Bavarian cuisine but the beer is spot on. You won’t be skipping any trips to Munich to come here, but it’s not a bad substitute for a Prost.
Anyone with a sweet tooth needs to look no further than The Milkshake Factory. Founded in 1914, the spot uses Pennsylvania milk to whip up indulgent shakes as well as tempting chocolates and other treats.
Where to Stay
The city’s downtown serves as a great jumping-off point for a Pittsburgh weekend getaway. My hotel pick is the Kimpton Hotel Monaco. It’s located right in the heart of the downtown with many spots (restaurants, shopping, the Andy Warhol Museum, and PNC Park) within walking distance.
The boutique hotel brand Kimpton is my go-to because it’s always fun. And today, the Kimpton Hotel Monaco Pittsburgh really captures the spirit of the city. Originally the Beaux Arts-style building housed an electric company in 1903. And now it’s full of colorful and spirited modern touches while still respecting and embracing the past.
In addition to being just the right size to get to know, a Pittsburgh weekend getaway is also relatively car-friendly. Visitors to Pittsburgh with cars will find it a useful tool for getting around the city if you decide to venture outside of downtown to Oakland or the South Side. There tend to be a fair number of garages and street parking options available. And weekend parking rates in the city’s garages are extremely reasonable when compared to other big cities. For metered street parking, the city has an app available that makes things easy and convenient.
Looking for more things to do? Just over an hour south of Pittsburgh is the Frank Lloyd Wright-designed home Fallingwater. Beautiful nestled amongst the trees and built directly upon a waterfall, Fallingwater is a great day trip from Pittsburgh.
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All photos, as well as all opinions, are my own. This post contains affiliate links.