What to do 8pm-midnight in Pittsburgh?

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Unless it's changed you don't have to walk to Station Square from downtown. Just walk up Grant Street to the Steel Plaza station of Pittsburgh's light rail system known as the T.

The T stops right at Station Square. Within downtown it's free. Not sure if the free zone extends to Station Square tho.

The T loops through the Golden Triangle's other station stops before crossing the Monongahela River to the Station Square stop. The Monongahela Incline, to/from the viewpoints on Mt. Washington, is right there as well. Highly recommended as long as you're in the neighborhood.
 
Unless it's changed you don't have to walk to Station Square from downtown. Just walk up Grant Street to the Steel Plaza station of Pittsburgh's light rail system known as the T.

The T stops right at Station Square. Within downtown it's free. Not sure if the free zone extends to Station Square tho.

The T loops through the Golden Triangle's other station stops before crossing the Monongahela River to the Station Square stop. The Monongahela Incline, to/from the viewpoints on Mt. Washington, is right there as well. Highly recommended as long as you're in the neighborhood.

The free fare zone on the "T" covers all of downtown and North Side ("Norseside"), from 1st Ave. to Allegheny stations. But not Station Square, just across the Monongahela. I think it costs $2.75 to get there from Steel Plaza. Not entirely sure, because the transit authority website makes it absurdly hard to find fare zones and because I haven't ridden that trip lately, it's well within my walking radius. (But not everyone's, I understand. And a visiting railfan would definitely want to take the "T" over the magnificent Panhandle Bridge!)

Panhandle Bridge (former Pennsylvania RR, now Pittsburgh "T")
 
The free fare zone on the "T" covers all of downtown and North Side ("Norseside"), from 1st Ave. to Allegheny stations. But not Station Square, just across the Monongahela. I think it costs $2.75 to get there from Steel Plaza. Not entirely sure, because the transit authority website makes it absurdly hard to find fare zones and because I haven't ridden that trip lately, it's well within my walking radius. (But not everyone's, I understand. And a visiting railfan would definitely want to take the "T" over the magnificent Panhandle Bridge!)

Panhandle Bridge (former Pennsylvania RR, now Pittsburgh "T")
You are correct. A ride to Station Square is outside the free zone and will cost $2.75. There used to be a much more confusing zone structure with longer rides costing more, but PRT eliminated that structure several years ago.. All rides on all buses and any ride on the T going south of First Ave (Station Square is the first station outside the free zone) are all $2.75.
 
Last time I did this connection I went to a German Biergarten on a roof somewhere within a six block walk of the station. I can't remember the name but it was rather nice. After that I ubered over to ride one of the inclines. And that about took the whole layover. Enjoy Pittsburgh it is the heart of Appalachia
 
Or "the Paris of Appalachia," in one local journalist's and adoptive Pittsburgher's memorable phrase.

https://www.amazon.com/Paris-Appalachia-Pittsburgh-Twenty-First-Century/dp/088748509X

Well another thing but I doubt you could do it in four hours there is Kennywood affectionally known as Kennyweird which is one of the last trolley parks left in the country. I believe there are only fifteen left and the majority of them are in Pennsylvania. They have some really unique and old school roller coasters with 3 coasters dating back to the roaring twenties. And who knows how long old rides like that have left so definitely something to do. A bit tough for a four hour layover, but definitely worth trying if you are a crazy coaster nut like me. They have a fast pass so if you went in with the mission of riding the credits you probably could do it in two hours.
 
Well another thing but I doubt you could do it in four hours there is Kennywood affectionally known as Kennyweird which is one of the last trolley parks left in the country. I believe there are only fifteen left and the majority of them are in Pennsylvania. They have some really unique and old school roller coasters with 3 coasters dating back to the roaring twenties. And who knows how long old rides like that have left so definitely something to do. A bit tough for a four hour layover, but definitely worth trying if you are a crazy coaster nut like me. They have a fast pass so if you went in with the mission of riding the credits you probably could do it in two hours.
Kennywood! Fellow roller-coaster buff here, and fan of classic rides like the Whip and the Turtle and Noah's Ark and the Parachute and the Kangaroo and the Bavarian; still mourning Laugh In the Dark. The coasters take advantage of Pittsburgh's topography. Favorite is the Thunderbolt, which dips deep into a ravine just across the Monongahela ("Mon") with an iconic view of the U.S. Steel's Edgar Thomson Works in Braddock, opened 1875 and still belching. Kennywood itself is on the National Register of Historic Places. The landscaping and the old-fashioned park buildings and gentler rides retain great charm.

Kennywood - Wikipedia

It's 11 miles and (optimistically) a half-hour from downtown, so I think doing it between trains is ambitious.

Chug out of Pittsburgh on the eastbound Capitol Limited early on a summer morning and you'll see the roller-coaster skeletons of Kennywood across the river in the ghostly dawn.

Fun fact: In local slang, "Kennywood's open" warns a gentleman that his fly is unzipped. Don't believe me, check the Urban Dictionary.
 
Kennywood! Fellow roller-coaster buff here, and fan of classic rides like the Whip and the Turtle and Noah's Ark and the Parachute and the Kangaroo and the Bavarian; still mourning Laugh In the Dark. The coasters take advantage of Pittsburgh's topography. Favorite is the Thunderbolt, which dips deep into a ravine just across the Monongahela ("Mon") with an iconic view of the U.S. Steel's Edgar Thomson Works in Braddock, opened 1875 and still belching. Kennywood itself is on the National Register of Historic Places. The landscaping and the old-fashioned park buildings and gentler rides retain great charm.

Kennywood - Wikipedia

It's 11 miles and (optimistically) a half-hour from downtown, so I think doing it between trains is ambitious.

Chug out of Pittsburgh on the eastbound Capitol Limited early on a summer morning and you'll see the roller-coaster skeletons of Kennywood across the river in the ghostly dawn.

Fun fact: In local slang, "Kennywood's open" warns a gentleman that his fly is unzipped. Don't believe me, check the Urban Dictionary.

I'll accept the challenge then to see if it is doable. I've been meaning to go there. A few weeks ago I did Holiday World in 90 minutes. Of course I'm not going to do it in conjunction with a train as I want to enjoy the park. But I want to see if I can do everything rapidly.
 
Well another thing but I doubt you could do it in four hours there is Kennywood affectionally known as Kennyweird which is one of the last trolley parks left in the country. I believe there are only fifteen left and the majority of them are in Pennsylvania. They have some really unique and old school roller coasters with 3 coasters dating back to the roaring twenties. And who knows how long old rides like that have left so definitely something to do. A bit tough for a four hour layover, but definitely worth trying if you are a crazy coaster nut like me. They have a fast pass so if you went in with the mission of riding the credits you probably could do it in two hours.
Looks like the park usually closes at 10pm during the summer, so by the time you got an Uber, made your way thru the gate, etc., you might have about an hour of ride time.

There is a bus from downtown, but it would get to the park at 9:20, which wouldn't be worth it.
 
True coaster buffs might try to make their connection from 43 to 29 on the NEXT day. Trying to squeeze a visit to Kennywood in same day is iffy, would require incredible luck, and wouldn't be worth it.

Splurge and get a hotel room, rent a car or use public transit, and spend significant time at the historic park. Plenty of time to do a few of the other Pittsburgh must-sees as well.
 
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