An Ideal Three-Day Getaway in Pittsburgh

Pittsburgh, Pennsylvania’s second-largest city, has long been cherished by its residents. Now, the word is getting out about its unique blend of gritty and quirky charm. Navigating the classic must-see spots along with the trendiest new restaurants, while also uncovering hidden gems, can be tricky without a guide. But don’t worry, we’ve mapped out everything you need to know and more.

So, lace up your comfortable walking shoes for a few days of delicious dining, cultural experiences, and crossing plenty of bridges. Here’s your guide to Pittsburgh for an unforgettable three-day weekend.

Day One

Upon arriving at Pittsburgh International Airport, you’ll enter the city through the Fort Pitt Tunnel—be sure to look up from your phone for your first breathtaking view of the skyline. It's a spectacular sight that never fails to impress, even for locals.

Check in at Kasa The Maverick, previously known as the Ace Hotel, or at Hotel Indigo in East Liberty. If you prefer to stay nearby for the evening, stroll down South Highland Avenue towards Shadyside, where you’ll likely encounter Muddy Waters, an oyster bar with a Cajun-inspired menu, and Mola, a casual sushi spot offering cocktails and bubble tea.

If you’re eager to explore further, take an Uber—a quick 10-minute ride—to Butler Street in Lawrenceville. Here, you’ll discover some of Pittsburgh’s best shopping; for unique ‘Burgh-themed gifts, clothes, and curiosities, be sure to visit Wildcard, No. 14 Boutique, and the balloon shop Von Walter & Funk. You might also want to check out Coven Brewing, a new addition to the craft beer scene founded by two Dancing Gnome alums.

When it’s time for dinner, you’re just a few blocks away from two of the city’s top dining spots. Visit The Vandal for a relaxed, contemporary American meal, or enjoy Spanish-style charcuterie and traditional pintxos at Morcilla. For a nightcap, head to Allegheny Wine Mixer for excellent wine in a cozy, living room-like setting, or dance the night away at Remedy or Spirit. Other fantastic cocktail venues include Bar Botanico in Lawrenceville and Bridges & Bourbon in the Cultural District.

Day Two

There’s no better spot to energize for a busy day than Pamela’s. Arriving at the Strip District location around 8:30 or 9:00 a.m. will help you avoid the crowds eager to dig into the diner’s renowned crêpe-style hotcakes.

Once you’ve wiped away any lingering syrup, take some time to explore the shops and Old World markets along Penn Avenue, where you’ll find locally made goods, gourmet snacks, and an abundance of Pittsburgh sports merchandise. Right next to Pamela's, you can rent a bike at the POGOH station — just $4 for every 30 minutes — and cycle towards the trail along the Allegheny River. This scenic route will lead you downtown to Point State Park, marked by a fountain at the convergence of three rivers.

You’ll pass four bike-friendly bridges, and the trail on the North Shore is stunning as well. If you're up for more cycling, the ride to Washington’s Landing is fantastic — about a 30-minute round trip along the river.

Once you arrive at the Point, take a moment for a photo op and a break by the fountain, then head to Market Square to return your bike and explore downtown. For an early dinner in a visually appealing setting, make a reservation at Tako or enjoy wood-fired steak in the Argentine style at Gaucho Parilla.

You’re ideally situated to catch a show or explore a gallery in the Cultural District, but for a breathtaking view, take the Wood Street T to Station Square and ride the Monongahela Incline to watch the sunset over the skyline from the overlook on Mt. Washington. If you have any romantic plans for your trip, this is the perfect setting.

From there, East Carson Street in the South Side — the city’s main nightlife hub — is just a short drive away, where lively bars like The Urban Tap keep the energy up until 11 p.m. or later. If you’re craving something a bit sweeter, The Milk Shake Factory down the street is open until 10 p.m.

Day Three

After a fulfilling brunch at Kelly O's Diner in the Hill District, take an Uber to the North Side to immerse yourself in contemporary installation art at the Mattress Factory or explore the works of Pittsburgh’s own Prince of Pop Art at the Andy Warhol Museum. If time permits, enjoy a leisurely stroll along the cobblestoned streets of the historic Mexican War District.

Finally, no visit is complete without diving into the Steel City’s famous sports culture. If you can’t snag tickets to a Steelers game, you’ll often find affordable bleacher seats for Pirates games at the stunning PNC Park. And if you indulge in a sandwich piled high with coleslaw and French fries from Primanti Brothers for dinner — available at both stadiums — you might just hit peak Pittsburgh.