CITY GUIDE: Pittsburgh

Pittsburgh typically doesn’t get mentioned in the conversation about the country’s top cities— but don’t expect to find a chip on the locals’ shoulders over that perception. Based on the conversations I’ve had while traversing the hilly scape, Pittsburghers seem content to keep their bounty a secret. 

But make no mistake: the Steel City has world-class food, architecture, and views to offer across a slate of highly walkable neighborhoods that rival those of its Northeast compatriots that are often heaped with much more attention. 

Grab a picnic and stroll to the edge of Pointe State Park in the heart of downtown to see, up close, the Allegheny and Monongahela rivers converge. Or take a ride up the historic Duquesne  Incline for that same view from above, compete with perspective of the bridges and city skyline. Buy insanely cheap, insanely fresh seafood on the Strip. Sip craft cocktails in East Liberty’s fresh new Ace Hotel. Or test the city’s next wave of restaurants in one of its incubator kitchens.

Best of all: Pittsburgh has authored its impressive turnaround following the collapse of the steel industry without harming the gritty spirit that bleeds through. It’s cool without pretension, full of quality finds without approaching extravagance. Don’t check the rental prices or else you might be enticed to stay.

In the meantime, here’s where you should eat, drink and play: 

Pointe State Park:

Thirty-six acres in the middle of downtown? Now that’s a city park. Marked by its signature fountain — blasting water 150 feet in the air — “The Point,” as its casually known, juts out into the intersection of the Allegheny and Monongahela rivers. If you’re a history buff, check out Fort Pitt and Fort Duquesne, two of the oldest structures in the city. But if you’re just there for the view, you won’t be disappointed. 

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Check out Pointe State Park here. 


Muddy Waters Oyster Bar: 

This Northeast meets Gulf Coast eatery celebrates a range of oceanic delicacies — starting with oysters (on the half shell or a garlicky roasted variety) is a must before choosing the rest of the meal from a cravings-laden menu. Lobster rolls? Check. Po’boys? Check. Shrimp n’ grits? Check. Soft-shell crab? Check. Then again, the small plates are pretty killer too — led by impossibly decadent hush puppies and deviled eggs stuffed with foie gras and topped with trout roe. Um, yes. 

Check out Muddy Waters here.


The Strip District

Before I first experienced the Strip, I anticipated that it would be very touristy. And, well, it is in a lot of ways. T-shirt and trinket stands line the streets. And yet somehow, the area along Penn Avenue has managed to hold onto its identity, too. Old-school markets — touting rare cuts of meat, whole rabbits, live bass, fresh cheeses and much more — at least equal the touristy spots. And some of the cities’ best new-wave eats and drinks are found tucked away on the side streets.


Check out the Strip District here, and see below for some of the district’s specific gems.


Robert Wholey & Co. (the Strip District):

Forget every other seafood market experience you’ve had outside of Japan: Wholey’s crushes them all. One of the Strip District’s anchors, founded in 1912, boasts tanks of live lobster and several kinds of fish — swimming seconds before you purchase them—as well as an almost unmatched selection of seafood and rarely seen cuts of meat, too. Grab a fried fish sandwich to snack on while you’re there, or visit the sushi bar. What else? There are singing stuffed cows and pigs stationed throughout the aquatic labyrinth, and a toy train zipping around a track built into the rafters. Just go.


Check out Wholey’s here.


Gaucho Parilla (the Strip District): 

Factor in waiting time — there’s usually a line winding outside from the counter, where patrons order. It’s worth it. The Argentinian fare, including daily empanada specials, steak plates, sausages and some seafood, is expertly done and reasonably priced. Most dishes come in a variety of sizes, so trying a lot of dishes without overloading on food is definitely possible. Bring your own beer or wine if you want (they don’t sell alcohol, but allow customers to bring it in), and know that the kitchen always appreciates extras.


Check out Gaucho Parilla here.


DiAnoia Eatery (the Strip District):

Find yourself transported to Coastal Italy at this charming Italian restaurant and bar, where you’re likely to contract a case of tile envy and possibly become overwhelmed by the level of cuteness in every detail (THE SALT AND PEPPER SHAKERS, COME ON). A full dinner menu is available, as well as takeout deli options. But just as attractive is the idea of sitting at the picture-perfect counter for an Instagram-worthy Aperol Spritz. 

Check out DiAnoia here.

Penn Ave Fish Co. (the Strip District): 

It’s not the sprawling wonderland that Wholey’s is, but this pared down fish market still has plenty to like, including sea urchin, soft shell crabs and stone crab when the season is right. Penn Ave also hosts an oyster happy hour from 4-6 p.m. on Wednesday through Saturday. BYOB! 

Check out Penn Ave. Fish Co. here.


La Prima (the Strip District):

Those who pop in for an espresso or freshly squeeze orange juice are just as likely to hear Italian spoken as English. Gray-haired men might be gathered on the sidewalk patio with their tiny cups, cigarettes and card games. Soccer might be playing on the small TV … è perfetto.

Check out La Prima here.


The Abbey on Butler:

Is The Abbey a bar? A bistro? A coffeehouse? Yep, all of the above, yielding a very interesting dynamic in the evening. Located on Butler St., Laurenceville’s vibrant main drag, the market-like space weaves together two bars, a casual eatery and a coffeehouse. In one room, shots are being taken; in the next, students hover over laptops and lattes. The centerpiece is a huge outdoor patio featuring a swan fountain. 

Check out the Abbey here.


The Ace Hotel:

Need more evidence that Pittsburgh’s star is blazing hot? Just head to the super hip Ace Hotel (it’s other locations include New York, LA, Chicago, New Orleans Portland, Seattle, Palm Springs Kyoto, Japan and London), which opened inside a former YMCA in 2016. Ace worked its magic again with quality food, coffee and style that incorporates the building’s history — look for old YMCA photos in the hall, a former rec hall transformed into meeting space and a summer-camp feel in the rooms.


Check out the Pittsburgh Ace Hotel here.



If you’re into the weird and the quirky, consider stopping by Randyland, home to a highly eccentric, very friendly man named Randy, who has essentially turned his house into a museum. Step into his yard, and you’ll find recyclables, mostly — things Randy has pulled from the trash and collected, painted and transformed into decor. It’s either art or junk, Randy says, depending on the critic. He leans more toward “junk,” but it clearly makes him happy, and chances are a quick stop by his ever evolving project will make you happy, too.

Check out Randyland here.


Church Brew Works:

Imagine a grand, century-old Catholic church, replete with stained glass windows, vaulted ceilings and dramatic arches. Now imagine massive tanks of beer on the place where the alter once sat, and a bar in place of the pews. Feel a little naughty? Well, maybe. But, the bartender pointed out to me, the church sold the space for this purpose, and conducted a ceremony removing all the sacred items from it. “So at that point, it’s just another building,” she said. Well, OK. The brew coming from the alter — boasting names like Pipe Organ Pale Ale and Pious Monk Dunkel — is no holy water. But the views alone make the brewery worth a stop. 

Check out Church Brew Works here.


Butcher and the Rye:

Come for the small, focused menu, the charcuterie, the knives as decor (the tap handles are giant cleavers) — or just set your sights on the wall of whiskey that towers behind the bar at this downtown spot. The inventive cocktails are well worth your time, too. 

Check out Butcher and the Rye here.


Duquesne Incline:

For the postcard view, take the Duquesne Incline up to Mount Washington. Yes, it’s the thing that *ALL* the tourists do, but it’s also kind of great. The near-vertical transport system first debuted in 1877 to help the miners get to the top of the steep hills and back down. Since being remade in the 1960s, it features a little red cable car, and runs throughout the day. Once you get to the top, grab your camera. The panorama, particularly for sunset or at golden hour, is stunning.


Check out the Duquesne Incline here.


Merchant Oyster Co.:

You’ll feel like you’re jumped aboard a ship at this purely Northeast Oyster Bar. The wooden tables are worn, as though they’ve been exposed to the wind and waves, the foot rest at the bar is a long, thick chain and food arrives in lightweight, camping-style dishes. Oysters and other raw bar options change daily; the menu is satisfyingly reserved otherwise, just a few seafood tins, served with crackers, and a handful of sandwiches. Wash it all down with a delightfully cold Vermintino — or go the boat route, and grab Narragansett in a can.


Check out Merchant here.


Federal Galley:

Here’s the concept: new, hopeful restaurateurs use the space, rent-free and essentially risk-free, paying a portion of their sales to the ownership. The result is a food hall, with four stalls, which rotate and a bar, which does not. Chefs can tuck money away, build a following and hypothetically momentum for eventually opening a brick-and-mortar restaurant, while the public benefits from new, changing options, while strolling around the market with a beer. Brilliant! Bonus, this North Side space is amazing. The ownership has another, smaller food hall with the same concept — Smallman Galley — in the Strip District.


Check out Federal Galley here.


Gateway Clipper:

In Pittsburgh, it’s easy to feel like everyone owns a boat. In the summer, the rivers are teeming with them. And with its steel cliffs and collection of colorful bridges (apparently there are over 400???), the views from the water are GOOD. If you can’t afford to charter your own, consider hopping aboard one of Gateway’s sightseeing or beer/wine tasting cruises. It’s a tour-like experience, but still nice to feel the wind on your face.

Check out Gateway Clipper’s cruises here.

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