Brooklyn Bridge Park
Holy hell, have you been to Brooklyn Bridge Park recently? It was rebuilt in 2010, and then rebuilt again after Hurricane Sandy, and it’s pretty incredible, especially the Pier 5 Picnic Peninsula. Complete with expansive views of Manhattan, grills for BBQ-ing (if you’re so inclined), and impeccable landscaping, Brooklyn Bridge Park has something for everyone, all under the shadow of the Brooklyn Bridge. If your ornery friends just can’t wait to get their drink on, start on the Manhattan side and pregame as you walk across the bridge.
Drink: Canned wine -- yes, it can be good, and it looks just like a can of soda. Check out Underwood or Alloy.
Tompkins Square Park
Ah, TSP... the nexus of all that is good and weird in this city. The park serves as a local hub for sports, tanning, and dog parades, but it hasn’t strayed so far from its history of illicit behavior that drinking here is out of the question. One of the best reasons to drink outside in this East Village oasis is that there are plenty of other bizarre behaviors to distract any law enforcement or local vigilante from your barely disguised alcoholic beverage.
Drink: Literally anything. You could probably wheel in a frozen margarita machine and turn a nice profit... and zero heads.