SummerSounds is a gem! A wonderful free music series in a natural amphitheater in a small downtown park. Excellent programming, sort of like a triple-A station, but more diverse. Lots of music that's new to me, but every time I enjoy it. Mostly $25 bands but it's FREE! Their sound system is AMAZING - by far best I've heard outdoors. Well-behaved crowd with many children and even some dogs. Lots of free parking within a block or two. Several good restaurants within 2-3 blocks.
Downsides: Park has "no alcohol" signs but no one seems pay attention to them. Smokers are restricted to one side of park and smoke drifts but it's bearable. Only on Fridays in June-August. It's beginning to get crowded as Pgh folks discover it so arrive by 6:30.