Location #6: House of Meadows’ mom
Unknown
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Location #7: Running out of…
Penn Station, 7th Avenue, Manhattan, New York, United States
Location #8: Park
Boston Common, Tremont Street, Boston, Massachusetts, United States
Location #9: The boys leave a restaurant
At 123 MacDougal Street, Manhattan, New York, United States
Location #10: New York Street
At 1251 Avenue of the Americas, Manhattan, New York, United States
The fight at the train station and them running away was filmed in Union Station Toronto,, They run out onto Front Street Toronto
The snowy Park is High Park, Toronto
The bar scene (I am the Shore Patrol!!!) was shot in The Little Bar in The Spadina Hotel at the corner of King St and Spadina Ave. The bar was identical until 1995 when they gutted it. The counter had cracks from Badass slamming his gun on it.
Google map of spot today. Lower left windows were where the bar was. Damn, I loved that bar.
https://bit.ly/2Sdt3zK
I think you took the location down from your list, but there’s a scene where the three men are walking near an El train and ARCO gas station, talking about going to a cathouse. That was shot in Boston, looking east along Berkeley Street (formerly Dover Street) towards the Washington Street Elevated. http://www.loc.gov/pictures/resource/hhh.ma1288.photos.075956p/
AFter the fight in the railroad station , they are clearly outside of Penn Station on 7th Avenue, New York CIty.