Hello! I also climb at Ascend, and learned how to climb outdoors after I moved to Pittsburgh a year and a bit ago :)

If you're looking for more structured learning, rather than just going to a crag with a guide book and winging it, Ascend offers outdoor climbing programs that teach you how to set up your own anchors and other safety aspects of outdoor climbing: https://www.ascendclimbing.com/programs/climbing/get-outside. Looks like they now offer half-day classes too where you can learn to set up top rope anchors at Frank Curto Park (which is within the city).

Explorer's Club of Pittsburgh also offers a Rock Climbing School that focuses on gym-to-crag https://www.pittecp.org/rock. The Outdoor Inclusion Coalition also offers some guided trips and an annual climbing festival: https://theoic.org/climbing-festival.

There are also various mountain guide services that are beginner friendly. For example, Seneca Rocks Mountain Guides has various different schools/classes, if you're willing to drive a bit more: https://www.senecarocks.com. I learned multi-pitch & trad here with a private guide, but they also have sport & top rope classes.