I used to drive to homestead shopping plaza where the AMC cinema is, park by eat n park and run the trail out of the city towards McKeesport. You run along a railway line, past the bottom of kennywood. If you want to go far enough you can cross the pedestrian bridge across the river into McKeesport. Cool run.

You could also park at Millvale and run along the river into and through the city all the way up to the old jail on the Ohio river and back. Could be a bit dicey though with all the encampments along that stretch of the river now, don’t do it near dusk or when there’s not many people around imho.