Technically I have been to Pittsburgh before, but honestly I remembered like nothing. So I am considering this “new”.
I took the kids on a trip just by myself. Pittsburgh is not terribly far from us and actually the drive is very much like 1/2 the drive to DC.
Each day we each picked things we wanted to do (from a list/or within reason), and we did that. There were a few snafus like that “bicycle heaven” was more than a few minutes away, we got twisted around driving, and showed up to a historical site that was closed.
But otherwise everyone got to have a little of the things they like and we had many fun adventures.
One surprising thing that happened twice was screenprinting. Warhol is from Pittsburgh and apparently we kept going places where randomly screen printing workshops were happening and we got to try it. My kids both enjoyed it and recommended we get our own speedball paint, pizza oven and screen.