After more than a decade working as a roofing professional across Western Pennsylvania, I’ve learned that roofing in Pittsburgh is its own category of work. The mix of steep hills, older housing stock, long winters, and constant freeze–thaw cycles exposes weak workmanship quickly. Roofs here don’t fail quietly. They show you exactly where corners were cut.
Early in my career, I worked on a re-roof for a family who couldn’t understand why water kept appearing near a second-floor window even though the shingles were less than three years old. The original installer had treated the job like a flat Midwestern roof—minimal ice protection, rushed flashing, and no attention to how snow slides and refreezes on steeper pitches. Once we stripped it down, the problem was obvious. Meltwater had nowhere to go but sideways. We rebuilt the valleys and flashing correctly, and the issue never returned.
One thing I’ve found is that Pittsburgh roofs punish assumptions. You can’t assume the deck is solid just because it looks fine from the attic. I’ve opened up plenty of roofs that hid soft spots near chimneys or additions where old leaks had been “temporarily” patched years earlier. Last fall, a homeowner was shocked when we found widespread rot under a section that had been boxed in during a remodel. Because we’d talked through that possibility beforehand, it wasn’t a crisis—it was just part of doing the job correctly.
A common mistake I see is homeowners focusing entirely on shingles. Shingles matter, but they’re only one piece of the system. I’ve seen expensive architectural shingles fail early because ventilation was ignored or underlayment was cut short in valleys. Pittsburgh winters don’t care how good your shingles look if warm air is trapped in the attic. That heat melts snow, the water refreezes at the eaves, and suddenly you’ve got leaks where no one expects them.
Experience also teaches you what not to do. I advise against any roofing approach that skips full tear-offs on older homes unless the structure has been properly evaluated. Layering new materials over old problems might save time, but it almost always costs more later. I’ve been the person called in to fix those decisions, usually after a heavy snow or driving rain exposes them.
Roofing here requires patience, planning, and a willingness to deal with what’s underneath—not just what’s visible. The jobs that last are the ones where the contractor respects Pittsburgh’s weather, its architecture, and the fact that this city doesn’t forgive shortcuts.