Squirrel Hill Theater
The former Babyland. Photo by Mike Machosky.

Babyland, corner of Penn Avenue and S. Negley, East Liberty

You know how Pittsburghers love to navigate by things that aren’t there anymore? “Yeah, hang a left by the old Jenkins Arcade, and go until you pass the old Isaly’s.” Well, people will call this corner Babyland (after the old children’s furniture shop) from now until the end of time. But for a number of years since Babyland closed, it’s been a big, abandoned eyesore on one of the most prominent corners in Pittsburgh. This spot is a hinge on which several neighborhoods with incredibly bright futures turn: East Liberty, Garfield and Friendship are all connected here. Supposedly, there are plans for a bank branch to go here, though nothing has happened yet. (Note for newcomers: This is not the Polish Hill music venue that has cheekily taken the name “Babyland” as its own). 

The former Froggy’s in Downtown Pittsburgh. Photo by Mike Machosky.
The former Froggy’s in Downtown Pittsburgh. Photo by Mike Machosky.

The former Froggy’s, Market Street, Downtown

This one is complicated. There’s currently a fight between the owners and preservationists about whether it should be knocked down. But it’s surprising that this beloved nightspot, which closed in 2003, didn’t quickly become a different bar or restaurant. Beyond its 1970s through 1990s heyday as a post-game gathering spot for Pirates, Steelers and Pens players, it’s an attractive 1898 commercial building. It shouldn’t have been left to rot for so long. 

The former Smithfield Cafe in Downtown Pittsburgh. Photo by Mike Machosky.

Smithfield Cafe, Smithfield Street, Downtown

In many ways, Downtown Pittsburgh is in better shape than it’s been in decades. The Cultural District used to feature a different kind of “culture” (it was a red-light district as recently as the ’80s). Still, there’s no shortage of empty eyesores Downtown, some of them huge. The former Frank & Seder department store, for one — though things finally seem to be happening there. But to pick out one particularly hopeless looking case, the Smithfield Cafe closed in 2012, and looks especially terrible — like an ashtray full of cigarette butts that nobody’s ever going to empty. It’s going to be a heavy lift to bring it back to life, but someone has to be up to the task. There was some interest a few years ago, says John Valentine from the Downtown Community Development Corporation: But, he tells us, “from what I understand, the building is in such bad shape, it most likely needs to be torn down.”

Empty building at the corner of Penn Ave. and Main St. in Bloomfield. Photo by Mike Machosky.

Penn Avenue and Main Street, Bloomfield

This is a total mystery. Penn and Main should be one of the liveliest corners in the city. And yet, that’s where you’ll find a weirdly wedge-shaped, beige brick building that’s as inert and empty as a PBR can cast aside from nearby Brillobox. Unlike most of the places on this list, this one showed serious signs of life five or six years ago. After a long period of abandonment, somebody went ahead and fixed up this spot in 2014 (or was it 2013?). Back then, it was looking look like a place with possibility, ready for a tenant. But … nothing. Years passed. Still, nothing. If you know the plan for this potentially cool space, we’d love to hear about it.

Michael Machosky

Michael Machosky is a writer and journalist with 18 years of experience writing about everything from development news, food and film to art, travel, books and music. He lives in Greenfield with his wife,...