Once the phenomenally wealthy center of America’s steel industry, Pittsburgh went through a rough patch after that industry collapsed. But the city is on an upswing now, with strong arts and business energy, and its striking steep hills and lush climate (similar to the Pacific Northwest) lend a beautiful natural backdrop.

A view of the Pittsburgh skyline and the city's funicular
A view of the Pittsburgh skyline and the city's funicular, which was built in the 19th century ©

Day 1

A colorful morning

Head to the North Side to visit the Andy Warhol Museum, a tribute to Pittsburgh’s pioneering pop artist that shows the full range of Warhol’s creative impulses. Nearby is the dazzling Mattress Factory, which has been showing contemporary art installations since 1977. One floor is devoted to light artist James Turrell. Afterward, stroll around the surrounding Mexican War Streets neighborhood to admire the artfully painted houses, or look for smaller pops of color at the National Aviary just south.

Lunch around the world

Head back south over the Allegheny River to graze in the Strip District, a former wholesalers zone that’s home to a super-diverse mix of food options. You might get enough to eat just from samples at grocers like Stamoolis (stamoolis.com) and Penn Mac (pennmac.com), but if not, fill up at Enrico Biscotti Café, which does excellent thin-crust pizza, or grab an epic Primanti Bros. sandwich, stuffed with French fries and coleslaw.

A true Pittsburgh original, this Primanti Brothers sandwich is stuffed with slaw and french fries.

Afternoon history lesson

Learn all about local Pittsburgh legends at the Heinz History Center, where city history is the focus. Did you know the Ferris wheel was invented here? And Rosie the Riveter, symbol of WWII women’s employment? And of course there’s that famous ketchup…

Dinner and evening bar crawl in Lawrenceville

The strip of land along the Allegheny northeast of the Strip District is one of the most dynamic and creative areas in the city – or, to say it more concisely, the hipster neighborhood. Start with dinner at Cure – if you want a splashy, multicourse meal of creative meat – or at Smoke BBQ Taqueria for a more casual dinner. Then work your way up (or down, depending where you started) Butler St, stopping off at various bars, such as Allegheny Wine Mixer, a great unfussy wine bar. If the weather’s warm, see what band is playing in the vacant lot next to Nied’s Hotel (and get a fish sandwich – a Pittsburgh favorite – if you’re still hungry).

Day 2

A very Carnegie morning

Industrialist Andrew Carnegie funded much of the city’s oldest, grandest infrastructure and cultural cornerstones. In the leafy old Oakland neighborhood, tour the adjacent Carnegie Museums. The art museum dazzles with European treasures and a huge collection of architectural models, while the natural history museum will wow kids with dinosaur skeletons and a beautiful exhibit of gems and minerals.

Cathedral of Learning at the University of Pittsburgh, the second largest academic building in the world.

Afterward, visit the University of Pittsburgh campus next door, where the Cathedral of Learning is a Gothic-look skyscraper that, in terms of the city skyline, puts education on the same level as business. On the first two floors are absolutely charming classrooms dedicated to different parts of the world, from Russia to Italy to Japan, and everything down to the chalkboards fits the theme.

Italian classroom at the Cathedral of Learning © Karen Blaha / CC by SA 2.0

Lunch for peace

Just south of the Cathedral of Learning, grab a hot lunch at the snack stand called Conflict Kitchen. Half art project, half restaurant, this operation has served everything from North Korean to Iranian cuisine, invariably good and home cooked. Don’t forget to read the food wrappers, with stats and interviews.

Afternoon tours

Spend the afternoon on the fringes – that could mean a tour of the abandoned Carrie Blast Furnace on the edge of the city, run by the local historical-preservation group Rivers of Steel. Or you could investigate the fringes of science at the Center for PostNatural History, a small but fascinating museum. Either way, make appointments ahead of time.

Sunset view and light dinner

Late in the day, visit the iconic infrastructure on Pittsburgh’s South Side: the Monongahela & Duquesne Inclines. These two funiculars, built in the late 19th century, are retro marvels and essential pieces of the city’s transportation network – plus, they’re a boon for tourists, as they offer fantastic views over the city. For a full loop, head uphill on the Mon, walk west on Grandview, have a drink and a burger at Altius, and head back down on the Duquesne.

Looking down on the inclined tracks of the Duquesne Incline from a viewing platform atop Mount Washington.
Looking down on the tracks of the Duquesne Incline from a viewing platform atop Mount Washington ©

Bluegrass by night

If it’s Wednesday, head back to the North Side for the Elks Lodge Banjo Night, a bluegrass singalong, and Park House, around the corner, for a somewhat more modern take on folk music. Otherwise, don’t leave the South Side before checking who’s playing at Rex Theater. Any night of the week, you can hit one of Pittsburgh’s classic, much-beloved dive bars, such as Gooski’s or Bloomfield Bridge Tavern; if you prefer cocktails, go for Kelly’s, in East Liberty.

Getting around

Driving in Pittsburgh can be tricky, with streets winding around hills and dead-ending suddenly; GPS can also be thrown off by the rapidly changing elevations. Ideally use the city’s extensive bus system, run by Port Authority Transit. It includes an express bus east from downtown, handy for the booming East Liberty area.

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