In local online running communities, I sometimes hear that people get bored on “hill” day, because they are tired of running the same hill week in and week out. Maybe they’ve chosen a specific hill in North Park or Schenley Park, or somewhere in their neighborhood and keep at it. Let me tell you, Pittsburgh has no lack of hills and there’s no need to run the same one all the time.
Take this run, for example. Beechview is about five minutes out of downtown, either through the Liberty Tubes to West Liberty Avenue or using the Fort Pitt Tunnels to Banksville Road. Park along on one of the broad residential streets, say Fallowfield Avenue. Within a mile, you’re likely to get a 100′ change of elevation. Do that a few times, and I think you’ll be set.
Fallowfield Ave 
You can see Mount Washington Buildings 
Rutherford Ave
Of course, if that doesn’t get your heart rate going, try a few staircases. There are plenty of them around here, too. Just don’t try the ones coming down to Goldstrom Avenue, unless you bring a rope. If the Rutherford steps or Belasco steps don’t tickle your fancy, cross West Liberty Avenue and go up Stetson Avenue or Ray Avenue.
Whoops, not these along Goldstrom Ave 
Rutherford at Broadway 
Belasco up to Broadway 
Stetson St 
Kenilworth and Brookline Blvd 
Fitzhugh 
Ray Ave Steps – one section
That’s about it. I’ve become fond of Beechview in spite of its ridiculous hills. Whittling down the streets, I only have about a dozen left there, maybe two or three miles and perhaps a half-dozen sets of stairs.