Two-Day Best of Pittsburgh Itinerary

Although a thorough exploration of Pittsburgh and its environs would require at least a week, the city is compact enough that its best sights and activities can be experienced easily in two days. The following itinerary assumes a Saturday-morning arrival in Pittsburgh; with the exception of a visit to the Strip District, which is at its best on Saturday mornings, the following activities can easily be shuffled around at will.

View of Pittsburgh skyline from Mount Washington

Day 1

Start your visit with an early-morning trip to the Strip District. Stop by Pamela’s Diner for breakfast and then join the throngs of shoppers searching for kitschy souvenirs along Penn Avenue.

Spend an hour or two at the Senator John Heinz History Center and browse in the gift shop on your way out; you’re unlikely to find a better selection of books about Pittsburgh anywhere else in the city.

If the weather is cooperating, treat yourself to a trip up Mount Washington on the Duquesne Incline—there’s a gift shop and small museum in the upper-level station—and then to one of the best views of the city along Grandview Avenue. The eastward walk along Grandview is one of the nicest strolls in town.

Continue on for just under a mile, pausing to enjoy the view from the large lookout platforms, to reach the Monongahela Incline, which you can ride back down to street level. Upon reaching the bottom, you’ll see Station Square just ahead—it’s a perfect pit stop for coffee or lunch. Should you find yourself in the mood for fine dining, head to Station Square’s historical Grand Concourse.

Afterward, make your way down East Carson Street toward the South Side Flats for a bit of late-afternoon shopping. Indulge in authentic Spanish cuisine at Mallorca, where fresh seafood and original recipes are the stars—try the paella.

Head back to the heart of the South Side Flats and end your day with a nightcap. Relax with a margarita on the rooftop deck at Local Bar + Kitchen, which also serves good pub grub.

Day 2

Weekend brunch at trendy Bar Marco is a good way to start your day. But if you’re only in the mood for a latte, wander over to La Prima Espresso instead and belly up to the coffee bar.

When it’s time to start moving again, take a long and leisurely stroll through downtown and into Point State Park, stopping off at the ToonSeum along the way. After you’ve seen the Point State Park fountain, use the pedestrian walkway on the Fort Duquesne Bridge to cross over the Allegheny River and into the section of the North Side known as the North Shore.

Head to the nearby Andy Warhol Museum, the largest single-artist museum in the United States. The Warhol has a great gift shop and a surprisingly good basement café, a great choice for lunch.

Next, head to the National Aviary in West Park, the only nonprofit bird zoo in the country. Spend the rest of the afternoon exploring the Oakland neighborhood. Take a self-guided tour of the Nationality Rooms in the Cathedral of Learning. All this exploration will leave you hungry, so stop by Fuel and Fuddle for their filling lunch options and excellent sweet potato fries. If the sun is shining, visit Schenley Park and its Phipps Conservatory and Botanical Gardens.

schenley park grass and flowers in front of Phipps Conservatory in Pittsburgh
Phipps Conservatory and Botanical Gardens inside Schenley Park. Photo © Christian Hinkle/123rf.

For dinner, head back downtown. Take a cab if the weather is chilly, or if you’re still on the North Side, go by foot across one of the Three Sisters Bridges. Your dining destination is Meat & Potatoes, a gastropub that dishes out simple but excellent American fare and legendary Prohibition-era cocktails.

After dinner, take in a show in the Cultural District. Pick up a free copy of the Pittsburgh City Paper to see what’s going on. If nothing grabs your interest or you’d prefer a less expensive and more intimate entertainment option, head back to the South Side via taxi and stop in at Club Café, which usually offers two pop or folk concerts nightly. (Ask your cabbie to take the 10th Street Bridge from downtown, which can also be crossed on foot.)

Emily King

About the Author

Emily B. King has been a Pittsburgher all her life. She graduated from the University of Pittburgh with a dual degree in English and Business, and moved to Squirrel Hill where she spent afternoons walking through nearby Frick Park and evenings sipping icy beers in Shadyside. Emily is an avid traveler and city girl, and her writing has been featured in The New York TimesMotherlode blog, XOJane, The Strip, LUX Magazine and Kidsburgh.org. She currently lives in the suburbs with her spouse.

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