Brewery wise I think starting at Necromancer for some unique beers, then a stop at grist house for some outdoor action and unique beers, then finishing at strange roots for a sour and some pittsburgh sandwich society might be the best brewery crawl possible. Wouldnt be hard to add hop farm, cinderlands, eleventh hour and/or trace from there either.

But if you are going to be in the south hills anyways, might want to keep it simple with spoonwood (great bbq too) and hitchhiker.

Sq hill has a new northern china eatery, amazing dumplings, that I recommend