In the Bakery Square area, you'll want to hit up The Galley for sure. Other good places include Tako, Brew Dog, Muddy Waters, Milkshake Factory and/or Millie's. For bars, check out Kelly's and Lorelie.

The Frick deserves a visit for sure! Lots of buildings/exhibits to walk through, and there's a nice little cafe on premises.

If you just wanna chill somewhere cool, my I recommend The Allegheny Wine Mixer (Lawrenceville), The Butterwood Bake Consortium (Lawrenceville), or Wigle Whisky (Strip District). Best eats around are probably Apteka (Bloomfield) and Pusadees Garden (Lawrenceville). Don't forget to get some pierogi too (Church Brew actually has some good ones, but the best can be found at random area churches).

Lawrenceville is probably your best bet for night life (bring your vaccination card!) - check out: Spirit (they have weekend bingo among other events), The Goldmark (dancing) and Belvederes (dancing, comedy, karaoke).

Most of the other things to do have been mentioned. I'd also recommend taking the incline up to Mt. Washington (do this at night for a classic experience) - bundle up and enjoy the view!