Hi all, Pitt alumni here and previous resident of San Francisco who attended a few Cal games when I lived out there. I'm currently live in DC but I am at all the Pitt games.
Hope you all come out. Couple of things to comment on in this thread.
1. Yes, Pitt's old on campus stadium was almost an exact duplicate of CMS...right down to Pitt's Cathedral of Learning peaking over the lip of the stadium like Sather Tower does. If they ever filmed a move about, say, Mike Ditka or Tony Dorsett or Dan Marino, they'd film it at CMS. But, it had to go for multiple reasons. Pitt's campus is very urban...not really anything like Cal's. The entire Oakland neighborhood campus is on less than 180 acres and it is bisected by two major roads and has the largest medical center in Pennsylvania crammed against it on one side and Carnegie Mellon University on the other. There are actually 6 universities within a 3 mile radius: Pitt, CMU, Carlow, Chatham, Duquesne, and Point Park.
2. Acrisure Stadium is a much more fan-friendly stadium and light years better for tailgating than the former Pitt Stadium was. It is about 3 miles from campus with shuttles running from the campus and pretty easy other public transportation. The atmosphere does struggle when Pitt is struggling, But should have 40-50K depending on how Pitt is doing, weather, and opponent.
You can see an overview of the facilities and campus here:
https://csnbbs.com/thread-564078.html. (please note, the section on places to eat around campus is outdated: COVID took a lot of them out). But if you are checking out the campus, the Cathedral of Learning and its nationality rooms are a must do. The city's main museums, the Carnegie museums (no relation to Carnegie Mellon University) of art and natural history, are also directly across the street from it.
3. Beer. Traditionally, it's an Iron City town. Honestly, it sucks unless you like Budweiser type pilsners. I personally don't know anyone that actually drinks it, but someone must because it is on tap everywhere. Rolling Rock is a watery mess and not brewed in Western PA anymore (was sold to Anheuser-Busch). Yeungling is on tap at every bar. It is a ubiquitous, cheap lager brewed in the east of the state and is actually still family owned and is America's oldest brewery (founded in 1812).
But there are MUCH better beers than these in Pittsburgh, that are actually brewed in and around Pittsburgh. Start with Penn Brewery, a German-style craft brewer that existed long before craft beer was a thing. But like every other city, craft brewing and distilling has exploded in the city. Heck, just go to these links:
https://pittsburghbreweries.com/ and
https://www.discovertheburgh.com/pittsburgh-distilleries/4. Food. I'm not going to BS you, SF was the best food city I've ever lived in, so don't expect Pittsburgh to match that. But Pittsburgh has some really good places to eat, don't get me wrong. The city's heritage is one of migrants coming int to take mill jobs in the 19th and early 20th century, so you have a heavy influence of eastern europeans (e.g., Polish). Definitely a pierogi town, and the Pirates have racing pierogi mascots.
Every city has their signature sandwich, and Pittsburgh's is a Primanti's. Is it my favorite? No, give me a philly cheese steak any day, but they are okay and you should try one at least once...and yes, it has fries and its own type of coleslaw on it. So you want to have a lunch like someone from the 'burgh, grab an Iron and a Primanti's.
BTW, the photo above of the Grand Concourse's Sunday Brunch...highly recommend it. Get reservations. Also for breakfast, try to hit up Pamela's (there is one on Pitt's campus), just be prepared for lines that stretch outside.
Otherwise, yelp is your friend like anywhere else depending on the type of food you are looking for.
5. Flying into or out of Philly. That is insane unless you want to spend extra days touring different parts of the state. I say that and I also lived years in Philly and drove to Pittsburgh for games all the time. The Pennsylvania turnpike... is terrible. There are actually a ton of things to do in and around Pittsburgh to fill up more than a weekend (see the above link) or the visit Pittsburgh website. DC or Baltimore would be easier to fly in and out of than Philly if you want to avoid the Pittsburgh airport for some reason (and you can take the historic Lincoln Highway a chunk of the way), but I'm not sure what reason there would be to avoid the airport unless there is a cost issue. I've never flown into Cleveland so can't comment on that. In any case, when coming in to the city from the Pittsburgh airport, you'll drive through the Fort Pitt tunnels...when you hit the tunnels, pay attention and you'll see why they say Pittsburgh is the only city with an entrance.