With its many artistic and culinary attractions, Pittsburgh, Pennsylvania, has become a top cultural center. Diverse neighborhoods connected by 446 bridges (more than any other city in the world) will give you a sense of choose-your-own adventure fun as you explore Steel City’s attractions.
You’ll visit the North Shore’s top museums, as well as the many cultural offerings in Oakland, home to the area’s universities. And don’t forget to save an entire afternoon for the strollable Strip District, where you’ll find the city’s best bars and restaurants.
As always, check for travel restrictions and closures before planning your trip.
Friday: Graze Your Way Through the Strip District
Your first day in town is all about discovering Pittsburgh’s food and spirits. That means you’re headed to the Strip District. First, stop by La Prima for a shot of espresso or an iced coffee topped with fresh whipped cream.
Then head to the Senator John Heinz History Center to learn about the city’s 250-year history. Don’t miss the museum’s Mister Rogers’ Neighborhood exhibit, which displays the largest collection of original items from the beloved television show (cardigans included).
In the early afternoon, go on a food tour with ‘Burgh Bits & Bites. You’ll get behind the counter at the historic market district’s finest bars and restaurants. The experience includes samples from some of the city’s many international restaurants — from Mediterranean and Polish cuisine to Italian pastries and cinnamon bread.
Next, take a seat at the Wigle Whiskey distillery. If you still have the energy, you can opt for a tour of the place. Or you can just relax while savoring a Sazerac or old-fashioned from one of the most awarded craft whiskey distilleries in the country. There’s also cider and a variety of beers on tap.
End your exploration of the Strip District with a visit to Coop de Ville, a Southern-style restaurant and bar offering fried chicken dinners made by chef James Ciminillo of the James Beard Award-nominated Richard DeShantz Restaurant Group. After dinner, linger a little longer to enjoy the restaurant’s arcade games, pinball machines and eight lanes of duckpin bowling.
Saturday: Find Fascinating Culture Downtown
Begin your day by exploring downtown Pittsburgh, where the Allegheny, Monongahela and Ohio Rivers merge. Though it’s the city’s business hub, it’s also an easily walkable borough. Begin with a visit to Point State Park, where you can stroll the park’s 36 acres of green space or bike the 24-mile riverfront trail.
Once you’ve worked up an appetite, opt for breakfast at the Speckled Egg. At this upscale diner located in the historic Union Trust Building, savor decadent dishes like the fried chicken biscuit and brown-butter French toast topped with strawberry-cardamom jam and maple syrup.
Then head to the Pittsburgh Cultural District for art and entertainment attractions, including theaters, live music and galleries. A highlight is the August Wilson African American Cultural Center, which offers galleries with site-specific installations, impressive collections of work by Black artists and a 492-seat theater.
In the afternoon, head to the North Shore neighborhood, the official home of Pittsburgh’s professional football and baseball teams. Sports fans can catch a game if the season’s right, and art lovers can browse the area’s world-class museums.
First, visit the Andy Warhol Museum, the largest museum in North America dedicated to a single artist. You’ll also love the museum’s architecture — it’s set in a former warehouse and distribution center, a fitting location to show the work of the Pittsburgh-born pop-art icon.
Next, head to the Mattress Factory, a contemporary art museum, before arriving at the Federal Galley, the area’s can’t-miss food hall. End your evening at Penn Brewery, the oldest and largest brewery in Pittsburgh, constructed by German immigrant brewers in the mid-19th century.
Brewing “craft beer” a century or so before the modern movement started, Penn also serves what it calls “ethnic Pittsburgh” fare, including wurst, pierogi and goulash, as well as area favorites like the “French Fry Salad.”
Sunday: Explore Art in Oakland
Home to Pittsburgh’s top academic institutions — the University of Pittsburgh and Carnegie Mellon University — the Oakland neighborhood is an epicenter of innovation and culture. Begin your day with breakfast at Pamela’s Diner, famous for its crepe-style hotcakes, croissants and French toast.
Then it’s off to explore the area’s many museums. Begin by visiting the Nationality Rooms located on the first and third floors of the University of Pittsburgh’s Cathedral of Learning, a 42-story skyscraper and the tallest educational building in the U.S. Within each of the rooms you’ll learn more about the diverse communities that call Pittsburgh home.
In the afternoon, visit the Carnegie Museum of Art to browse some of its 34,000 pieces, representing the intersection of art, architecture, photography and design. Explore exhibits like the archive of negatives of the late Pittsburgh photographer Charles “Teenie” Harris, known for recording an intimate look into Black life in America.
Nearby is the Carnegie Museum of Natural History, where you’ll learn about dinosaurs, gemstones and the world of botany. If you still have time to explore, don’t miss the Phipps Conservatory & Botanical Gardens. On the site’s 15 acres of flourishing green space, stroll past lady slipper orchids, Japanese bonsai and desert plants like the saguaro.
To close out your weekend in Pittsburgh, book a table at Spirits & Tales, a brasserie located at the top of the Oaklander Hotel. Toast to your trip over steak and frites with views of the glittering lights of the Oakland neighborhood below.
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