How to Spend a Weekend in Pittsburgh

Duquesne Incline (Photo: Visit Pittsburgh)

By Kalena Thomhave

August 22, 2022

With its stunning views, world class museums, and pierogies, Pittsburgh has a lot to offer visitors.

The city of Pittsburgh may evoke images of steel mills with tall smokestacks or make you think of industrialists like Andrew Carnegie and Henry Clay Frick. While the Pittsburgh of 2022 is still proud of its robust steel history — you’ll still see the names “Carnegie” and “Frick” everywhere — it is also a great place to stay for a weekend. 

Once you spend some time here, you’ll see why this city of 445 bridges—more than Venice, even though we lost one this year — has been consistently named a “most livable city” by The Economist.

Friday Afternoon

If you can, enter the city through the Fort Pitt Tunnel on I-376 for an immediate and stunning city view welcoming you to Pittsburgh.

But no matter how you get here, you should take some time on your first afternoon to get yourself oriented to the city. You can get fantastic views of the Pittsburgh skyline and all of its bridges from Mount Washington, a neighborhood atop a hill on the southern shore of the Monongahela River. The best way to get to the top of Mount Washington is by incline. An incline—technical term funicular—is a cable railcar. Pittsburghers of yesteryear used to travel up and down the city’s surrounding slopes by a number of inclines, though today just two remain. 

The one we recommend, the 145-year-old Duquesne Incline (1197 W Carson St.), will take you up with other tourists and commuters for a small fee. At the top, you can take some time to poke around the small museum in the upper station and visit an observation deck to take some panoramic photos of Pittsburgh, before hopping back on the incline to return down the hill.

Friday Night

Continue your introduction to Pittsburgh by enjoying some classic Pittsburgh foods. When first considering tourist activities in Pittsburgh, you might have heard that you’re supposed to get a sandwich with french fries on it. If you’d like to try this cultural icon, visit any of the city’s several Primanti Bros. outposts for a sandwich piled high with meat, cheese, coleslaw, and fries. For a taste of history alongside your meal, visit the original Primanti’s restaurant in the Strip District. 

READ MORE: The Ultimate Comfort Food: 5 Places to Get Pierogies in the Pittsburgh Area

Prefer to eat off the beaten path? Seek out pierogies—dumplings filled with potatoes and other fillings—a perennial Pittsburgh favorite thanks to early Eastern European immigrants. Apteka (4606 Penn Ave.) in the Bloomfield neighborhood, a sit-down restaurant with a casual yet hip vibe, serves pierogies, other Eastern European food, and craft cocktails.

Saturday Morning

Pete Seeger may have once sung about how Pittsburgh is a “smoky ol’ town,” but the thick smog of Pittsburgh’s industrial heyday has since lifted. So, get outdoors! There are numerous trails to explore, like the Three Rivers Heritage Trail, which winds around the city center and all three rivers. You could also rent a kayak or paddleboard to discover the city by water—there are three nearby rivers, after all—through an outfitter like Kayak Pittsburgh. If you’re visiting in the colder months, you can still enjoy time outside. We recommend Schenley Park, which has an ice-skating rink in the winter.

In the afternoon, keep enjoying the outdoors by eating takeout in the sun. Schenley Plaza (4100 Forbes Ave.), near the University of Pittsburgh, has a number of food stands where you can get your lunch to-go and then lounge in the grass or at a patio table in the shadow of the university’s 42-story Cathedral of Learning.

If you’d rather just visit a restaurant to eat, try The Porch at Schenley (221 Schenley Drive) near the plaza, where you can enjoy fresh, seasonal food indoors or out.

How to Spend a Weekend in Pittsburgh
Photo: Jin Wu

Saturday Afternoon

The city has a number of world-class museums where you might spend your afternoon. For a museum experience that rivals those you might find in bigger cities like New York, head to any of the Carnegie Museums. The Carnegie Museum of Art (4400 Forbes Ave.) and the Carnegie Museum of Natural History (4400 Forbes Ave.) sit next to each other in the Oakland neighborhood, near the University of Pittsburgh and Schenley Park. You can pay one fee to visit both so that you can pair your Van Gogh viewing with a peek at dinosaur bones. Another Carnegie museum, the Andy Warhol Museum (117 Sandusky St.) on Pittsburgh’s North Side, hosts the largest collection of work by Warhol, a Pittsburgh native.

For a more offbeat experience, try Bicycle Heaven (1800 Preble Ave.), a free bicycle museum also on the city’s North Side. Bicycle Heaven has thousands of bikes crammed into its rooms, including historic bikes and famous bikes like the one from Pee-wee’s Big Adventure.

How to Spend a Weekend in Pittsburgh
Photo: Dave DiCello

Saturday Night

Depending on the season, you can remind yourself you’re in the “City of Champions” by going to cheer on one of Pittsburgh’s sports teams. The Pittsburgh Pirates baseball team or the Pittsburgh Penguins hockey team may be playing on the Saturday you’re in town. Wear black and gold, as all three major professional teams in the city rep these colors. 

While the Pirates may not be doing too hot, at least they play at a ballpark with one of the best views in the MLB—PNC Park. (It’s tough to get tickets for Pittsburgh Steelers football games on Sundays—the team has sold out every home game since 1972—but if you’re a passionate football fan you could make buying a resale ticket part of your itinerary.)

Prefer to watch a game with smaller stakes (and smaller ticket prices)? Pittsburgh also has a USL soccer team, the Riverhounds, that plays on the shore of the Monongahela River.

How to Spend a Weekend in Pittsburgh
Photo: Jody Mader

Sunday Morning

Close out your weekend in Pittsburgh with a visit to the Strip District, a diverse and lively neighborhood that’s home to many of the city’s international grocery stores and eateries. The Strip District (Smallman Street and Penn Avenue between 11th Street and 33rd Street) used to be an anchor of Pittsburgh industry, and you’ll still notice some of that history as you walk the shops and admire the architecture.

You can grab breakfast in the Strip at the ever-popular Pamela’s Diner (60 21st St.), famous for their Lyonnaise potatoes and crepe-like pancakes. If you’d rather not wait—because the line will almost certainly be long at Pamela’s—try the also-popular Kelly-O’s Diner (100 24th St.). 

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