The perfect long weekend in Pittsburgh, Pennsylvania

Once the vibrant heart of America’s industrial sector, Pittsburgh has transformed from a city dominated by smoky steel mills to a hub of lush parks, renowned universities, and leading medical facilities.

In the 19th and 20th centuries, waves of immigrants seeking job opportunities flooded into hilly neighborhoods such as Polish Hill, Deutschtown, East Liberty, and Allentown. Today, these lively areas stand as a testament to Pittsburgh's incredible Rust Belt transformation.

My partner is a proud “Yinzer” – a local from Pittsburgh, where the endearing term “yinz” replaces “y’all.” Over many visits, the ’Burgh (also known as the Steel City or the City of Bridges) has captured my heart.

Here’s my ultimate guide to making the most of your time in Pittsburgh over one unforgettable long weekend.

Best time to visit: I suggest planning your trip between May and October (winters can be harsh here). Arrive by plane or car on Thursday evening, and head back home on Sunday evening.

Transportation from the airport: A taxi or rideshare will cost around $55–70 and will get you to Downtown in about 20 minutes. Alternatively, the 28X-Airport Flyer bus takes about half an hour at a much lower cost.

Getting around the city: Downtown Pittsburgh, known as the “Golden Triangle” due to the convergence of three rivers, is compact and easy to explore on foot. For accessing nearby neighborhoods, taxis or rideshares (or your own vehicle) are the most convenient options, although Pittsburgh Regional Transit does offer a network of public buses and three light-rail lines. Notably, the agency operates two funiculars that ascend to Mt. Washington, providing stunning views of the Downtown skyline—a must-see during your visit.

Accommodation options: Downtown offers a variety of hotels, but be cautious as many impose steep parking fees. An economical boutique choice, Joinery Hotel Pittsburgh, has rooms priced between $120 and $167, along with a rooftop terrace and bicycle rentals. Just across the Monongahela River, the Priory Hotel features 42 rooms in a former monastery, with rates ranging from $150 to $230. Parking is complimentary, and the Monks’ Bar is a fantastic spot to relax.

Packing essentials: Bring layers! For the spring and fall days and evenings ranging from 50° to 70°F, having options is key. During summer, it’s typically t-shirt weather when temperatures rise. Additionally, it's wise to pack something waterproof for those rainy days.

Friday

Morning: Begin your day with a light breakfast, perhaps a vegan pop tart, at Gasoline Street Coffee Company. Once energized, enjoy a half-hour walk through Downtown and along the Allegheny River Walk to the Andy Warhol Museum. This repurposed factory showcases multiple floors of paintings, photographs, films, and more from the legendary Pop Art artist, who hails from Pittsburgh.

How to spend the day: After visiting the Warhol Museum, explore the Strip District for lunch. This area, once industrial, has transformed into a vibrant hub of street vendors, shops, restaurants, and bars, with historic buildings now home to coworking spaces and trendy apartments.

Prepare for tasty delights like a spicy mung-bean pancake straight off the griddle at a Chinese food stall. Alternatively, enjoy a salad with fresh mozzarella at the Pennsylvania Macaroni Company, a bustling Italian market serving pasta since 1902. Once you’ve satisfied your appetite, head to the Heinz History Center, which boasts more than just ketchup exhibits. Here, you can see Smithsonian-level artifacts like the world’s oldest Jeep and learn about Pittsburgh’s rich history.

Dinner: Stay in the Strip District into the evening. Local landmark Primanti Brothers, which began as a food cart in the 1930s, is now famous for its submarine sandwiches loaded with coleslaw and fries—originally designed as a convenient meal for hungry railway workers. Wrap up your night with a grappa or rye whiskey at Kingfly Spirits Distillery or savor a dram of cask-aged bourbon at Wigle Whiskey Distillery.

Saturday

Morning: Get ready to pedal! Begin your day downtown at Bae Bae’s Cafe, enjoying a light breakfast sandwich on a warm croissant before renting your bike at Golden Triangle Bike.

How to spend the day: As you cycle along the Monongahela River, witness Pittsburgh’s shift from an industrial hub to a green city. Remnants of the industrial era are visible everywhere: bike past The Workers, a pair of sculptures crafted from reclaimed steel, and head towards the lush South Shore Riverfront Park, which has transformed from a steel mill barge dock into a lovely rest area.

Cross the Hot Metal Bridge to reach Triangle Bar and Grill, where you can grab a hoagie sandwich fit for a steelworker – like the impressive Battleship, measuring a full 26 inches. (If you're not feeling quite so adventurous, go for the smaller Triangle Destroyer.) After that, ride to the Rivers of Steel National Heritage Area and take a tour of the historic Carrie Blast Furnaces, picturing the many workers who labored in this tough environment. Conclude your unique Pittsburgh day at Point State Park, where the Monongahela and Allegheny Rivers meet the Ohio River. Relax on the grass by the fountain, enjoy your hoagie, and watch kayakers and anglers on waters that were once nearly toxic.

Dinner and after dark: Church Brew Works in Lawrenceville is set in a repurposed church, with house-brewed beers like Blast Furnace Stout paying homage to its heritage and the area's working-class roots. Ordering delicious dishes like pierogies, chorizo meatballs, or vegetarian spaghetti is a perfect excuse to linger and sample more brews.

Sunday

Morning: After a night of enjoying craft beers, you're going to need a hearty breakfast the next morning. Fortunately, the weekend brunch at Sally Ann’s features the Pittsburgh Nasty, a delicious buttermilk biscuit piled high with fried chicken and pork, crowned with an egg and drenched in sausage gravy. In other words, it's the perfect remedy for your morning cravings.

How to spend the day: On a serene Sunday, there's nothing quite like a leisurely stroll through the 23 gardens and 14 Victorian-style greenhouses of Phipps Conservatory. You'll journey from the humid paradise of the Orchid Room to the arid landscape of the Desert Room. Outside, take in the tranquil ponds and a collection of water lilies that could inspire a Monet painting. Keep the peaceful vibe going with lunch at Café Phipps.

If you have some extra time, don’t miss the breathtaking Cathedral of Learning, just a 10-minute stroll away. This stunning 42-story Gothic Revival structure looms over the University of Pittsburgh campus like something out of a Batman comic. Join a guided tour to admire the exquisite craftsmanship and church-like ambiance of its classrooms, labs, and faculty offices, making for a perfect conclusion to your Pittsburgh weekend.