A Long Weekend Guide to Art and Culture
3 Days In Pittsburgh
So you're visiting Pittsburgh for a long weekend. If you've never been, you're in for a surprise! You’ve looked at our maps, did some googling, and left more overwhelmed at what to do than ever. Let us make it easy for you! Read below for a touch of Pittsburgh history followed by a pre-planned guide of places to eat, drink, and visit in the City of Bridges.
Gone are the days when Pittsburgh was dubbed "hell with the lid off". Today, the city is a phoenix reborn, having risen from its industrial ashes to become a vibrant hub of culture, innovation, and gastronomy. With award-winning chefs setting up shop in restored historic buildings, and a brewing + distilling scene that is gaining fame, with 76 breweries & counting, the Steel City is crafting a new identity, one pint and plate at a time.
Nestled where three rivers meet, Pittsburgh boasts not only a rich history but also a present that's bursting with energy. Panoramic views from Mt. Washington, art installations that echo the city’s storied past, and green spaces that stretch as far as the eye can see, all tell the tale of a city that values both its heritage and its future. And it's not just about the views; the sounds of live music, the tantalizing aromas wafting from food stalls, and the hum of conversations at local coffee shops create an ambiance that's unmistakably Pittsburgh.
Dive in, embrace the Yinzer spirit, and let this guide lead you through three days of discovery in a city that seamlessly blends tradition with modernity. Whether you're here to relish the culinary delights, imbibe in craft brews, or simply soak in the city's scenic beauty, Pittsburgh promises an experience that will linger long after you've left its bridges and tunnels behind. And now, let’s embark on a journey through the heart and soul of this ever-evolving city...
3 Day Itinerary
Arrival Day
Classic North Side Pittsburgh
Neighborhoods: North Side, Downtown
You roll into town in the early afternoon. Start with a cultural experience, and venture to the Andy Warhol Museum. Immerse yourself not only in the art but also in the interactive Silver Clouds installation—a dreamy room filled with floating silver balloons. If you haven’t had enough eclectic art, head over to Randyland from here – a wild explosion of colors and funk.
If the art and walking have worked up a thirst, swing by the Federal Galley food hall for cocktails & local beer. They offer a variety of great pop-up-style dining options. If you're more into breweries, then Allegheny City Brewing is your spot. After a few libations, make your way to Fig & Ash on the North Side (don’t forget to make a reservation!)
If you’re still amped up and raring to go after dinner, head across the bridge (it’s a 20-minute walk or 3-minute Uber) to The Warren. It’s unassuming from the outside (and even on the inside at first!) but it’s an amazing dive-vibe spot for mezcal, amaro, or a world-class cocktail. Finally - get yourself an Uber and head back to your HostWise property for a comfortable night’s rest.
Full Day 1
Foodie Vibes in the Strip & Steel City Views
Neighborhoods: Strip District, Oakland, Mt. Washington, South Side
Kick off your morning with a French press of freshly ground Cieba Commonplace Coffee, right in your home (we’re the exclusive carrier in Pittsburgh!) Then, head to Pamela’s Diner for a decadent breakfast. While they’re renowned for their crepe-style pancakes, don't miss their Lyonnaise potatoes — they’re a crispy, seasoned delight! Stick around and enjoy the rest of your morning in the Strip District, keeping an eye out for iconic locales like Penn Mac, a go-to for imported cheeses and cured meats. There’s something for everyone in the Strip! Then, grab lunch at the OG Primanti Bros. Huge, well-known sandwiches with fries & coleslaw piled high – and of course, don’t skip getting an “Ahrn” (Iron City Beer) with your meal. We’re fans of the Capicola & cheese (and add a fried egg, of course).
After the frenetic pace that can be the Strip, slow it down a bit, and head to the Phipps Conservatory and Botanical Gardens. Their tropical gardens make you forget that you’re in the middle of a bustling city. If slowing down isn’t your style, then the Church Brew Works beckons next; try their Celestial Gold lager, a light brew that pairs well with their pierogi pizza—a true Pittsburgh fusion!
Late in the afternoon, it’s time to head up the hill - the Monongahela Incline offers a piece of Pittsburgh history, as one of the few “funiculars” left in the country. Plan B - an Uber or Lyft is a less scenic, but quicker route to the top. Once atop Mt. Washington, the view is breathtaking from any of the viewing platforms. On the way across, stop in any of the bars on Shiloh St for happy hour. Then for dinner, Altius offers more than just a stunning skyline view; their seasonal menu is always can’t-miss.
After quite the day, if you’re still in need of a night cap - wind down at Acacia on the South Side - a speakeasy vibe slinging bespoke cocktails all night long.
Full Day 2
Outdoors, Arts & Lawrenceville Nightlife
Neighborhoods: Downtown, Oakland, Lawrenceville
Start your morning at The Commoner with a Bloody Mary. We’ve never had a bad meal here, and since you’re in Pittsburgh you’ve gotta go for the Pierogies & Kielbasa. If you need to walk it off for a bit, head back to the North Side and wander the Three Rivers Heritage Trail. Keep an eye out for the unique sculptures that dot the route—each tells a story of the city's legacy. In the afternoon, consider visiting the Carnegie Museum of Art and Natural History. Boasting one of the best collections in the country, you can easily spend hours immersed in its culture.
As evening rolls in, Dinner at Morcilla in Lawrenceville awaits. Piloted by an award-winning chef, their Spanish-influenced cuisine pairs perfectly with a glass (or two) of sangria. Post Morcilla, take a stroll down Mulberry Way and admire Jeremy Raymer’s street art.
From here, head north to Eleventh Hour Brewery for an IPA or sour beer, then to the Grapperia for a well-deserved digestif. If you're still buzzing with energy though, dancing at Spirit is in order – it feels like an 80s firehall wedding every night on the weekend. Don't leave without trying their late-night pizza, served in a nostalgic, cafeteria-style setting. If you’re still raring to go after this day…you have more energy than the rest of us combined.
Departure Day
Bidding the ‘Burgh Adieu
Neighborhoods: Strip District
While it’s always tough to say goodbye, there’s still a chance for one last culinary journey. Prior to heading home, stop by Cinderlands in the Strip for brunch. An award-winning brewery on its own, their culinary team pulls out all the stops for brunch. We’re big fans of the smoked pastrami sando paired with a sour Whipper.
