The Distillery District might be on the touristy side as locations go but it does have alcohol for Gooshin and a mix of indoor and outdoor locations for those that might be intimidated by the weather. Some of the shops don't allow photography inside but outdoors, common areas and the bars should be fair game.
I could make it for any time on the 22nd and don't have a strong preference on timing.
If I'm reading the map Panoguy posted correctly there's a bakery just inside the entry gate to the Distillery at Mill St. and Trinity St. that would be a good place to meet in front of. It's building 45a on this map:
http://www.thedistillerydistrict.com/Map_2009.pdf and I believe it's called the Brick Street Bakery.