Introduction Depending on how hardcore you are, you can skate outdoors year-round in the city. The prime season is April though October, but even in the depths of January and February, there will be some very skateable weekends with temperatures in the 40s. All you can really hope to do in such weather is simple stuff. I'll leave that decision to you. Just remember, be sure to drink some water or Gatorade at frequent intervals and consider carrying a water bottle or Camelbak.
Few things are worse than a nice day of skating wiped out by a case of heatstroke.
Okay, let's admit it. When you walk into the Grand Central Station and see that glorious expanse of sa-moooooth marble floor interrupted only by the info kiosk in the middle, your toes start itching to do some rolling. Well, you're not the only one who feels that way, and I've known people to sneak in and skate the station and other famous places, like the World Trade Center concourse. Thus, if you feel like you just have to try skating a famous place, be prepared for adverse legal consequences. Another on-line resource is Transalt's Fiboro Bridges , which you'll find very helpful if you're trying to figure out how to get from one borough to another without using the subway.