The Midwest City that Boasts Some of the Quirkiest Museums in the U.S.

To the untrained eye, or casual passerby, Pittsburgh has largely been regarded for its French fry sandwiches, its bridge-strewn rivers, its swing-state influence, and its ironclad Steelers fans (and, ya know, the industry that earned Pittsburgh the nickname “Steel City”). Nowadays, aside from the amount of screen time given to campaigning politicians, Pittsburgh has diversified its cultural stew considerably, to include a wealth of attractions, museums, green spaces, and amenities—old and new, high and low.

Of late, Steel City has evolved into the destination for Rust Belt reinvention, brimming with new ideas, new restaurants, and new museums touting the glories of pop art and the homegrown Big Mac. It’s a place where modernist and Victorian architecture share turf with Frank Lloyd Wright masterworks (and a laudable collection of green-certified buildings), where major festivals run the gamut from Oktoberfest dachshund races, to one of the world’s largest annual furry conventions. It’s a place where beer-drinkers bump elbows with cocktail connoisseurs, where the food scene offers so much more than bucket list sandwiches, and where art-lovers are just as dazzled as stand-up paddle boarders and wannabe inventors.

While it would be all too easy to distractedly spend two months getting lost in Pittsburgh and all its seasonally changing riches, here’s how to maximize two days away in this uniquely American river city.

2 hours and 15 minutes from Cleveland
4 hours and 15 minutes from D.C.
5 hours from Philadelphia

Singular museums can be found in cities across the globe, but not too many places can lay claim to institutions touting such disparate cultural titans as Andy Warhol, Mister Rogers, and the world’s most famous hamburger. And Pittsburgh is the only place where you can tackle all three in one casual afternoon.

Effectively Pittsburgh’s own artsy Graceland, The Andy Warhol Museum celebrates one of America’s most influential visual artists, in the town where he grew up. Long before he rose to superstardom in New York City, and before his Factory left an indelible mark on Manhattan’s social scene, he was but a humble Pittsburgher, coming of age during the Great Depression. Although he didn’t rise to fame in his hometown, nor spend much time there after high-tailing it to NYC, his roots never left him. Certain works, like his portrait of Andrew Carnegie and his Heinz Tomato Ketchup Box, harken to Pittsburgh icons. His namesake museum, with rotating exhibits and frequent events, contains the largest collection of Warhol’s art and archives in the world, including the popular Silver Clouds exhibit that features floating metallic balloons.

As Warhol’s Heinz Tomato Ketchup Box suggests, Heinz Tomato Ketchup also calls Pittsburgh home. And it inspired the naming of the Heinz History Center, a multifaceted history museum that goes way beyond condiments with its vast array of exhibits for visitors of all ages. Mister Rogers fans young and old can check out the display of the original set and items from the children’s show, including the entryway and living room where Mister Rogers would lace up his sneakers. Other exhibits detail Pittsburgh’s pre-steel days as Glass City, and a display of local inventions, from the Polio vaccine to the lunar rover. Of course, there’s also an 11-foot ketchup bottle if that’s what you’re really here for.

And speaking of ketchup, you can go right to the source at Pittsburgh’s own Big Mac Museum Restaurant, a North Huntington McDonald’s specially designed to celebrate the birthplace of the world’s most famous/infamous hamburger. The aptly “super-sized” eatery features all manner of McD’s memorabilia, like a vintage sauce gun, a bronze statue of Big Mac inventor Michael Delligatti, and of course, a 14-foot Big Mac.

One of the most popular outdoor activities in the city, and the one that affords the best skyline views, is to ride an incline. Known around the world more commonly as Funiculars, these are a pair of steep railways that ascend Mount Washington, looming over the city on the south shore of the Monongahela River. Both inclines, the ketchup-colored Duquesne and the mustard-colored Monongahela, started as commuter rails for residents in Mount Washington. Today, they’re still used as such, but they’ve also become iconic attractions for tourists looking for sweeping views of one of America’s most underrated skylines.

In addition to the Monongahela River, the two other rivers that intersect in Pittsburgh are the Allegheny and Ohio Rivers—which, altogether, make for plentiful aquatic attractions. Among them, the Gateway Clipper Fleet offers dining and sightseeing cruises, while those looking to work up more of an appetite can rent paddle equipment from local outfitters like Surf’s Up Adventures and Venture Outdoors.

The best ways to drink in the views, though, are on foot, from one-of-a-kind vantage points like Point State Park. The 36-acre park, which sits at the nexus of the three rivers, contains an iconic fountain, the Great Lawn, and ample walking and cycling trails. Downtown, historic Market Square—constructed in 1764!—is in the center of the hustle and bustle, where commuters criss-cross with festival-goers, pop-up events, holiday markets, and customers flocking to adjoining restaurants and shops.

From April to October, it’s both baseball AND carousel season in Pittsburgh. Located in Schenley Park, the PNC Carousel is a Victorian-style installation that boasts lively colors and old-fashioned organ music. The original carousel was located at the intersection of Panther Hollow Road and Greenfield Avenue in 1913, before being re-erected and moved to its Oakland location in 2006. Carousel rides are $2, and family season passes are available.

Get to know what gave the Steel City its nickname on a Carrie Furnace Tour, which highlights iron-making technology, what the workers were like, and the gone-but-not-forgotten steel industry culture that Pittsburgh was once steeped in. There’s something for everyone with these tours, whether you're a history buffs, artist (arts and ground tours), an outdoorsy types (discover how nature reclaimed the landscape on a tour led by an area botanist), or curious about the machines (guided machine shop tours). 

As you’re piecing together by now, Pittsburgh is the home of many inventions, from life-saving vaccines to life-changing condiments. Inventionland is a 60,000-square-foot work environment where area inventors work on the next big idea to change the world. Inside the giant warehouse are unique themed sets for inventors to work in, like pirate ships, treehouses, and more, and it’s fun to see the creative process pop up all around you. However, if you go on a tour note that photography is expressly prohibited. So, oompa- loompa-doopity-don’t post a pic on social media.

Breakfast: Sweet tooths can’t resist “the Greatest Cake in America”—the burnt almond torte at Prantl’s Bakery—but you can’t go wrong with whatever you eat here. Enjoy Kaufmann’s Thumbprints cookies that come in more than 60 flavors, or pretend you're getting married to sample wedding cakes and prepare cookie tables.

Pittsburgh has no shortage of sterling brunch options, but if you’re truly unable to decide, you can’t go wrong at Square Cafe, a beloved Highland Avenue diner which features local artwork on the wall and ceramic square mugs for drinking delicious java. Unique dishes include blueberry hush puppies, Brussels sprouts hash, and tofu muffulettas.

Lunch: The ‘Burgh may be known for Primanti’s sandwiches and putting French fries on everything, but its oldest bar and restaurant is The Original Oyster House, located in Market Square. First opened in 1870, The Original Oyster House is a designated historic landmark and represents much of what modern-day Pittsburgh is about, fusing respect for history with delicious cuisine. Old photos and Pittsburgh memorabilia line the walls and evoke a charm that makes you feel like you’re traveling back in time.

For sandwiches that are somehow even more unique than those topped with French fries, hit up this envelope-pushing food-truck-turned-restaurant, Stuntpig. Expect elaborate riffs on classic comfort food flavors, like a pulled chicken sandwich with spicy piri piri and chimichurri aïoli, a crab cake sandwich with grilled lemon and Old Bay aïoli, and a Moroccan meatball sub.

Dinner: For a full-fledged farm-to-table experience, make the quick trek to the suburbs to dine at Hyeholde. From its pastoral locale on four acres of land, the restaurant is able to procure its own produce and harvest its own honey, resulting in an ever-changing spree of seasonal dishes from chef Chris O’Brien, like an autumn squash soup with pistachio-cherry granola, venison carpaccio bruschetta with squash butter, and chestnut pasta with apple cider-braised pork and marrow butter.

A longstanding Mediterranean mainstay, Casbah boasts a cozy interior reminiscent of a wine cave, and an airy year-round patio. Wherever you’re supping, you’ll be well-fed on dishes like mussels, grilled Spanish octopus, saffron pappardelle, and grilled swordfish.

New to the prolific portfolio of restaurants from the Richard DeShantz Restaurant Group, this bustling Japanese izakaya arrives mid-October in the East End, complete with a transportive facade designed to conjure a sense of Tokyo pub culture. In true izakaya fashion, the snacky food menu at Golden Gai features shareable plates like sushi and edamame, plus sea urchin noodles, pan-fried pork dumplings, and charcoal-grilled fish.

Drinks: It’s not Bavaria, but it’s still pretty wunderbar. Hofbräuhaus Pittsburgh emulates Munich’s original brewhouse concept with German bier, live entertainment like polka bands, servers in traditional garb (bring your lederhosen), and a picturesque view of the river. You can dine outside in the biergarten that overlooks the waterfront when it's warm, but no matter the time of year, this is always an ausgezeichnet place to go.

Pittsburgh has a thing for turning old buildings into bars, whether it’s a funeral parlor (The Abbey) or even a YMCA (The Maverick hotel). Church Brew Works was one of our first restaurants with a former history, as it used to be St. John’s the Baptist Church. Today, vats of beer sit on the used-to-be altar and you can dine where pews used to be.

It’s the friggin’ Allegheny Wine Mixer, located in Upper Lawrenceville! From the outside (and maybe even the inside), this Step Brothers-inspired bar doesn’t look like anything Dale and Brennan would ever drink at, but there are little homages to the 2008 comedy, like the name of the establishment and the Incredible Hulk Hands above the bar. The cheese toasties complement the wine selection like, well, Boats ‘N Hoes.

For something totally different, intimate Lawrenceville haunt Grapperia is an Italian bar spotlighting grappa and amari. Complete with an attached Italian wine shop, the whole vibe does a great job convincing you into thinking you are, indeed, ambling into an adorable wine bar in the Italian countryside. You’ll find pitch-perfect requisites, like an Aperol Spritz, alongside novelties like the LaVanda, made with lavender-infused grappa, green peppercorn honey, lemon juice, and pea flower.

The Maverick by Kasa: Formerly The Ace Hotel, and before that a YMCA, this East Liberty boutique features just 63 meticulously designed guest rooms and suites, with a well-preserved facade that channels the building’s turn-of-the-century architectural grandeur.

The Industrialist Hotel: This aptly dubbed Pittsburgh property, harkening to Steel City’s heyday, is situated in a historic Beaux Arts building downtown, dating to 1902. Today, the 18-story property offers pet-friendly rooms and suites, along with its Maker Menu—a nightly assortment of DIY projects, like leather-stamping and candle-making, available to guests and would-be inventors.

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