The Porch, Oakland. Aside from the Point and the overlooks on Mt. Washington, this might be Pittsburgh’s most iconic setting—in the shadow of the Cathedral of Learning, on a soft green expanse between the largesse of the libraries (Carnegie and Hillman). The Porch’s profusion of patios includes an impressive stone fireplace for chilly nights and an unobstructed view of college town Pittsburgh, where you can nap on the lawn between classes at “Cathy” like the future is still ahead of you.
Istanbul Sofra, Regent Square. The earthy, rich aroma of grilled meat and Turkish spices fills the air inside Istanbul Sofra, which is surprisingly free of the fumes from South Braddock Avenue. (Pittsburghers inexplicably think that street is the Autobahn.) It’s partially shielded by a wall of plants and fruit trees, big umbrellas and strings of tiny flags. Save room for baklava.
Rivertowne North Shore, North Shore. This part of town still seems unfinished more than a decade after its redevelopment started. But one thing that was done right was the riverfront edge, which is oriented entirely toward the water. All the restaurants here overlook that postcard view of The Point. To pick just one, Rivertowne makes some good beers, and is an all-local operation, surrounded by chains.
Redfin Blues, Washington’s Landing. Somehow Redfin Blues, which overlooks a marina on the Allegheny, had Pittsburgh’s rivers all to itself for the longest time. (Remember when it was Troll’s?) Located on the island of Washington’s Landing, Redfin is a great spot to dine on the water from the deck overlooking the marina. The menu sticks to the basics, plus lobster rolls and “all-you-can-eat Alaskan Snow Crab Clusters” — and the beer selection is quite good.
Spirit, Lawrenceville. Nightclub, concert venue, superior pizza place—is there anything Spirit can’t do? They’ve got a very nice, and very spacious back patio, too, for when your ears are ringing and you just need to clear your head.
Nicky’s Thai Kitchen, North Side. The best Thai restaurant in town? Maybe! Pad Phet and Pineapple Curry aside, there’s a narrow brick patio out back, bedecked with a small jungle’s worth of tropical greenery. Nicky’s Thai Kitchen is about as intimate as an outdoor space gets—not a bad spot for a date, unless one of you goes to one of the other locations (about a mile away, Downtown, or way up on Mt. Nebo Road.).
Meat & Potatoes, Downtown. It’s hard to say when Downtown Pittsburgh really, finally became an actual destination for great food. It might have been before Meat & Potatoes, but the restaurant was the icing on the cake (or the fat on the bacon, or something . . . ). Everything about this place is built to last, from the simplicity of the menu to the huge amount of space devoted to outdoor dining. Right in the middle of the booming Cultural District, this is a great place to people-watch, with as many well-dressed theater/symphony patrons as mustard-stained Pens jerseys.
Six Penn Kitchen, Downtown. One of the first places in Downtown Pittsburgh where you could get on the roof without picking a lock, Six Penn was also instrumental in the culinary revival of Downtown. The trees up there are full-sized now, offering some shade.
Roland’s Seafood Grill & Iron Landing, Strip District. One of the best people-watching perches in Pittsburgh is right above Penn Avenue at Roland’s in the Strip. It seems like everybody in Pittsburgh—and boatloads of tourists—all want to get their cheap groceries and bootleg Stillers’ gear at the same time—and the bustle is a sight to see. Plus, you can eat big pots of mussels or “Hot Lobster Roll Sliders” while taking it easy on the large second-floor balcony.