The Ultimate Pittsburgh Long Weekend Guide

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. The 19th and 20th centuries saw immigrants drawn by the promise of jobs, arriving by the hundreds of thousands, filling the hilly neighborhoods like Polish Hill, Deutschtown, East Liberty, and Allentown. Today, these vibrant areas testify to how Pittsburgh has become 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 captured my heart.

Here’s my guide on how to make the most of your time in Pittsburgh during an ultimate long weekend.

When to Arrive

May through October is the ideal time for a visit (winters here can be brutal). Fly or drive in on Thursday evening and head home on Sunday evening for a fulfilling trip.

Getting to the City

To get from the airport, a $55–70 taxi or rideshare will take you to Downtown in around 20 minutes. Alternatively, the 28X-Airport Flyer bus makes the journey in about half an hour for a fraction of the price.

Navigating Downtown

Downtown Pittsburgh, also called the “Golden Triangle” where three rivers converge, is compact and walkable. For reaching surrounding neighborhoods, taxis or rideshares (or your own car) are the easiest options, although Pittsburgh does operate a network of public buses and three light-rail lines. The funiculars, which ascend to the top of Mt Washington, offer spectacular views of the Downtown skyline and are a highlight of any visit.

Where to Stay

There are many hotels Downtown. However, many come with hefty parking fees. Affordable boutique options like the Joinery Hotel Pittsburgh, range from $120 to $167 per night and offer a rooftop terrace and bicycle rentals. Across the Monongahela River, the Priory Hotel is a unique 42-room boutique hotel that was originally a monastery, with rates between $150 and $230. Parking is complimentary, and the Monks’ Bar is a great place to unwind.

What to Pack

• Layers for 50°F–70°F days and evenings during spring and fall.
• T-shirts for the hotter summer months.
• Waterproof gear for potential damp days.

Friday Overview

Morning

Kick off your Friday with a light breakfast, such as a vegan pop tart at a local coffee shop. After fueling up, take a stroll through Downtown and over the Allegheny River Walk to the Andy Warhol Museum, which showcases the work of the renowned pop artist and Pittsburgh native.

Day Activities

After visiting the museum, venture into the Strip District for lunch. This area has transformed from industrial roots into a vibrant hub of street vendors, shops, restaurants, and bars. Sample exciting delights, like a spicy mung-bean pancake or a salad with fresh mozzarella from a busy Italian market. Following your meal, explore the Heinz History Center, which provides a deeper understanding of Pittsburgh’s rich heritage through various exhibits.

Dinner

Stick around the Strip into the evening for a local culinary classic. Primanti Brothers is famed for its hearty sandwiches filled with coleslaw and fries. Conclude your night with a drink at one of Pittsburgh’s distilleries, where you can enjoy local grappa, rye whiskey, or craft bourbon.

Saturday Overview

Morning

Start your Saturday by enjoying a breakfast sandwich before renting a bike for the day. As you cycle along the Monongahela River, you’ll witness the continued transformation of Pittsburgh from an industrial to a green city. Keep an eye out for art installations and parks situated along the route.

Day Activities

Stop for a hearty hoagie sandwich at a local spot before heading to the Rivers of Steel National Heritage Area for a tour of the historic Carrie Blast Furnaces. This experience offers a glimpse into the city’s industrial past, reminding visitors how Pittsburgh came to be known as the Steel City.

Dinner and Nightlife

Experience the Church Brew Works in Lawrenceville, located in a decommissioned church. Sample delicious beers and enjoy a menu that pays homage to the city’s working-class past while enjoying dishes like pierogies and chorizo meatballs.

Sunday Overview

Morning

After a night of sampling craft beers, indulge in a fulfilling breakfast that features a buttermilk biscuit piled with fried chicken and pork, topped off with an egg and smothered in sausage gravy—just what you need to start the day.

Day Activities

Spend a leisurely Sunday strolling through the beautiful gardens and greenhouses at the Phipps Conservatory, then relax by the peaceful ponds. After soaking in the serene environment, enjoy lunch at the onsite café.

Final Exploration

If time allows, explore the iconic Cathedral of Learning at the University of Pittsburgh, marveling at the stunning architecture. It’s a perfect conclusion to your enriching long weekend in Pittsburgh.