48 Hours in Pittsburgh

Day One

Morning

Begin your trip with breakfast at the hotel’s Terrace Room, an opulent dining area dating back to 1916 that serves up a variety of benedicts, grilled dishes and breakfast entrees. Consider the Art of Breakfast buffet, which offers made-to-order eggs and omelets, breakfast potatoes, fresh fruit, sausage and bacon, yogurt, cereals, artisan breads and pastries, smoked salmon and cereals.

Another option about a mile from the hotel is DeLuca’s Diner, a staple breakfast spot located in the Strip District. This popular spot, featured on Travel Channel’s "Man Vs. Food," is worth the wait for menu items that include breakfast burritos, crepes, fancy pancakes, waffle sundaes, oversized omelets and the famous “mixed grill.”

While in the Strip District, make sure to take the time to shop around. Originally an industrial neighborhood, the area has been revamped, with specialty stores and international vendors moving in to the iconic brick buildings. With grocers from Italy, Poland, Asia and the Middle East, you’ll find every product you need from abroad, while other retail stores sell varied teas, cookware, jewelry, chocolate and throwback candies, spices, dried flowers, clothing, metal art and more. 

Afternoon

Stick around for lunch, as the Strip District has plenty to offer foodies. Though not technically a restaurant, Pennsylvania Macaroni Company—lovingly called Penn Mac by the locals—is a great spot to gather food for a picnic. Put together your own charcuterie platter with artisanal cheeses from around the world. Pair them with the shop’s deli meats, olives, dried cherries and apricots, Italian crackers and plenty of dips and spreads then head outside to eat. If you’re looking for something a little heartier, the Strip District is also home to the original Primanti Bros. sandwich company. Here, you can try the eatery’s version of the famous Philly cheesesteak, the Pitts-Burger and Cheese.

Heading southwest along the Allegheny River, you’ll come across the Heinz History Center, named for Senator John Heinz. Affiliated with the Smithsonian Institution, this is the state’s largest history museum, detailing prominent events with a local connection through interactive exhibits.

On the way back to the hotel, you’ll pass Bike The Burgh Tours. This tour company is one of the best ways to see Pittsburgh, with offerings like the Beauty of the Burgh tour, which highlights all of the city’s must-sees, as well as specialty tours focused on things like local bridges, ballgames or food and drink.

Evening

After freshening up for dinner, pay a visit to the on-site Wigle Tasting Room and Bottle Shop for pre-meal drinks. Snag a flight of whiskey or craft a build-your-own Old Fashioned. While there, you can explore the bottle shop for gifts for friends and family back home or for bottles to enjoy during the rest of your vacation.

When it comes to dinner, there are two riverside options that offer stellar views and delicious food. First up, Altius is a chef-driven New American restaurant a few miles from the hotel that offers everything from steak tartare, tuna carpaccio and chilled oysters to lamb loin, King salmon and grass-fed strip steak. 

The alternative, LeMont Restaurant, has stunning views of the river and the Pittsburgh skyline as well as live music. The Continental cuisine at LeMont includes two specialties for couples, twin steak filets or beef tenderloin meals prepared tableside.

After dinner, a visit to the Duquesne Incline is a must. The sloped railroad scales Mount Washington with a ride in an old-fashioned cable car that is more than a century old. The station at the top of the incline contains a museum with historic photographs and information, but the most spectacular part of this experience is the unbeatable view.

Day Two

Morning

Enjoy a morning with breakfast in bed. Omni William Penn Hotel offers room service that can make for a relaxing experience, with fluffy pancakes being one of the menu’s highlights. Take your time getting ready before heading out for the day.

Or, if you’d rather eat somewhere nearby, Bluebird Kitchen makes a great option. Within walking distance of the hotel, the bakery boasts an ever-changing seasonal menu and dishes that are made almost entirely in-house to ensure freshness.

Walk off some of your breakfast calories with a trip across the Allegheny River via the Roberto Clemente Bridge. Also known as the Sixth Street Bridge, this impressive suspension bridge is one of three that crosses the river. Painted gold, the bridge’s arches frame the city beyond for photographs while the views from the walkway of the water and the skyline also make for picture perfect vistas.
 
Directly across the bridge, you’ll find two museums worth visiting: the Andy Warhol Museum and the Mattress Factory. Warhol was born and raised in the city so the museum is a dedication to his life and artwork, serving as the largest museum centered around one specific artist in the country. With 17 galleries on seven floors, it contains more than 12,000 works by Warhol, including photographs, paintings, films and sculptures. The nearby Mattress Factory is another space filled with contemporary artwork, though it is of a different nature. Completely installation-based, guests can enjoy pieces that were designed specifically for the space they’re in.

Afternoon

For lunch, visit the Italian eatery Sienna Mercato. One part meatball joint, one part wine bar and one part rooftop beer garden, the atmosphere of this spot can’t be beat.

From there, take a stroll around the historical Market Square, which is about a half mile away. This area is home to regular events like farmers markets, outdoor concerts, flash mobs, educational programs, yoga classes, dance lessons and cultural fairs, and has been an important gathering spot throughout the city’s history.

Another option is to instead head over to the area near the University of Pittsburgh to dine at The Porch at Schenley. Focusing on local ingredients and causal fare, the airy atmosphere on the patio is perfect for enjoying a crisp salad, a hot pizza, juicy burgers or a variety of sandwiches.

If you have lunch at The Porch, you’ll be close enough to the Phipps Conservatory and Botanical Gardens to explore for a while. This historic landmark is a verdant oasis in the middle of the city, with more than 20 gardens and a 14-room greenhouse. In addition to seasonal flower shows, guests can examine sustainable architecture, green gardening practices, commissioned exhibits and special flower collections.

Evening

On your last night in Pittsburgh, go for a pre-dinner drink inside the hotel at The Speakeasy. This Prohibition-era bar, tucked beneath the hotel lobby, has been restored to its former glory. Enjoy a house classic Manhattan and enjoy the vibe reminiscent of the Pittsburgh of the 1920s.
 
Next, head next door for dinner at Union Standard. The modern eatery, which is located in the historic Union Trust Building, offers a seasonal menu of fare inspired by the northeast, the Mid-Atlantic and the Appalachians, namely seafood and wood-fired rotisserie dishes.
 
After dinner, make your way to the Cultural District and explore the local art galleries. If you’re lucky, you’ll be in town during the quarterly gallery crawls, which brings the whole community together with art showcases, live music, film screenings, theater performances and creative hands-on activities. If not, there are still plenty of galleries to visit, including SPACE, Emmanuel Fine Art Photography, the 707 Gallery and Wood Street Galleries.

Then, enjoy a nearby show at one of the local theaters to end the night right. Both The Benedum Center for the Performing Arts and the Byham Theater offer stage shows, while Cabaret at Theater Square is the ideal place to take in a comedy show or enjoy live music.

If you have more time...

Sports are an important part of local culture and Pittsburgh has great sporting venues and a hardcore fan base. If you have some spare time, take in a Pirates baseball game, a Penguins hockey game or a Steelers football game.

For a step back in time, places like Old Economy Village or nearby Smicksburg offer a glimpse at how others live right here in our own country. While the village preserves the lifestyle of the Harmony Society, Smicksburg will teach visitors about the Amish lifestyle.

The Omni William Penn Hotel concierge team contributed to this article.