The New York City Inline Skating Guide
Where to Skate: 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.
When the temperature gets down to about 30°F, light layers covered by some sort of windproof outer garment seem to do the trick . I've found that a T-shirt, sweater or ski vest, lightly padded windbreaker, "Drylete" tights, light gloves (under wrist guards), bandanna and a helmet suffice when added to the usual skates, socks, and armor; if the sun is out and it's not windy, you can even ditch the windbreaker. However, as the temperature falls below 30°F, muscles and skate wheels become less responsive so that artistic and trick skating become much more difficult than usual. All you can really hope to do in such weather is simple stuff.
On the other hand, when the temperature is over 80°F, the streets and bikepaths will be swarming with skaters, many of whom may be pushing the limits on how much skin they can safely and legally expose. 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 place However, such activity publicly-owned locations is probably illegal, and at corporate/privately-owned places, they may consider unauthorized rollerskating to be trespassing. Thus, if you feel like you just have to try skating a famous place, be prepared for adverse legal consequences.