The ultimate long weekend in Pittsburgh, Pennsylvania

Once the beating heart of industrial America, Pittsburgh has evolved from a city of mighty, pollution-spewing steel mills to one of green parks, talent-attracting universities and world-class medical centers.

In the 19th and 20th centuries, immigrants drawn by the promise of jobs arrived by the hundreds of thousands, packing into hilly neighborhoods like Polish Hill, Deutschtown, East Liberty and Allentown. Today, these vibrant areas testify to how Pittsburgh has emerged as a remarkable story of Rust Belt transformation.

My spouse is a “Yinzer” – a native of Pittsburgh, where people charmingly say “yinz” instead of “y’all” – and over years of visits, the ’Burgh (or Steel City, or City of Bridges) has won me over.

Here’s my guide to how to get the most out of Pittsburgh in one, ultimate long weekend.

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When to arrive: I’d recommend visiting between May and October (winters here can be brutal). Fly or drive in on Thursday evening, then head home on Sunday evening.

How to get from the airport: A $55–70 taxi or rideshare gets you to Downtown in 20 minutes. The 28X-Airport Flyer bus makes it in half an hour for a fraction of the price.

Getting around town: Downtown Pittsburgh – also called the “Golden Triangle,” as it’s the point where three rivers meet – is compact and walkable. To reach surrounding neighborhoods, taxis or rideshares (or your own car) are easiest – though Pittsburgh Regional Transit does operate a network of public buses and three light-rail lines. The agency’s two funiculars, which ascend to the top of Mt Washington and its killer views of the Downtown skyline, are a highlight of any visit here.

Where to stay: There are numerous hotels Downtown – but be warned that many hotels charge hefty parking fees. An affordable boutique option (rooms range from $120 to $167), Joinery Hotel Pittsburgh has a rooftop terrace and bicycle rentals. Across the Monongahela River, the Priory Hotel is a 42-room boutique hotel that was originally a monastery; single rooms range from $150 to $230. Parking is free, and the Monks’ Bar makes a great hangout.

What to pack: Layers! For the 50°–70°F days and evenings of spring and fall, you’ll want options. Summer, when temperatures can soar, is t-shirt weather. And it’s always a good ideal to pack something waterproof for damp days.

Friday

Morning: Start with a light breakfast like a vegan pop tart at Gasoline Street Coffee Company. Fueled up, take a half-hour stroll through Downtown and over the Allegheny River Walk to the Andy Warhol Museum. This converted factory fills several floors with paintings, photos, films and much more by the Pop Art master, a Pittsburgh native.

How to spend the day: After the Warhol museum, snack your way across the Strip District for lunch. This is a formerly industrial area where warehouses and railway lines have given way to street vendors, shops, restaurants, and bars, with historic buildings now housing coworking spaces and trendy apartments.

Look forward to delicious surprises like a spicy mung-bean pancake hot off the griddle at a Chinese food stall. Or choose a salad with fresh mozzarella at the Pennsylvania Macaroni Company, a busy Italian market that’s been slinging pasta since 1902. After you've eaten your fill, make your way to the Heinz History Center. Billing itself as “more than a ketchup museum,” the Heinz History Center displays Smithsonian-worthy artifacts like the world’s oldest Jeep, as well as exhibits that tell the history of Pittsburgh.

Dinner: Stick around the Strip into the evening. Local landmark Primanti Brothers started as a food cart in the 1930s – and is now universally known in the area for its submarine sandwiches packed with coleslaw and fries, originally an all-in-one meal for hungry railway workers. Finish things off with a grappa or rye whiskey at Kingfly Spirits Distillery or a dram of cask-aged bourbon at Wigle Whiskey Distillery.

Saturday

Morning: Prepare to get pedaling. Start downtown at Bae Bae’s Cafe for a light breakfast sandwich on a toasted croissant before renting your ride at Golden Triangle Bike.

How to spend the day: As you follow the Monongahela River, you’ll get a sense of Pittsburgh’s transformation from industrial to green. Signs of the industrial past are everywhere: you’ll bike past The Workers, a pair of sculptures made from reclaimed steel, and toward grassy South Shore Riverfront Park, built on the site of a steel mill barge dock and now a nice spot for a rest stop.

Cross the Hot Metal Bridge to the Triangle Bar and Grill to pick up a hoagie sandwich worthy of a hearty steelworker – like the Battleship, which is a full 26 inches long. (If you’re not feeling brave, opt for the half-size Triangle Destroyer.) Next, cycle to the Rivers of Steel National Heritage Area and tour the old Carrie Blast Furnaces, imagining the thousands of workers sweating out their jobs here. End this only-in-Pittsburgh day at Point State Park, where the Monongahela and the Allegheny Rivers converge into the Ohio River. Settle on the grass near the fountain, unwrap that hoagie and watch people kayak and fish on waters that were once near-toxic.

Dinner and after dark: Church Brew Works in Lawrenceville occupies a deconsecrated church, and house-made beers like Blast Furnace Stout nod to this heritage, as well as the neighborhood’s working-class past. Ordering tasty fare like pierogies, chorizo meatballs or vegetarian spaghetti is an excuse to stick around and sample more beers.

Sunday

Morning: An evening of craft beers calls for a filling breakfast the morning after. Luckily, the weekend brunch at Sally Ann’s includes the Pittsburgh Nasty, a buttermilk biscuit loaded up with fried chicken and pork, topped with an egg and smothered in sausage gravy. In other words, just what the doctor ordered.

How to spend the day: On a quiet Sunday, few things beat a stroll through the 23 gardens and 14 Victorian-style greenhouses of Phipps Conservatory, which will take you from the steamy jungle of the Orchid Room to the dry-as-a-bone Desert Room. Outside, gaze at the peaceful ponds and a display of water lilies worthy of a Monet painting. Continue the reverie with lunch at Café Phipps.

If time permits, one last must-see sight is just a 10-minute walk away. The showstopping, 42-story, Gothic Revival Cathedral of Learning presides over the University of Pittsburgh campus like something out of a Batman comic. Take a guided tour to see the fine craftsmanship and church-like interior of its classrooms, labs and faculty offices for a fine ending to a Pittsburgh long weekend.