South Side of Union Square, across from Whole Foods, where you see all the skaters getting ready
Whether you're a lifelong New Yorker or a transplant, there's nothing quite like the freedom of skating through traffic in a group on NYC streets. This event has been going on for years and to my knowledge, is perfectly safe. Not sure about your skating skills, support bikers welcome! This event is rated beginner as far as we're concerned (truly for all levels of physical fitness), but "intermediate" for the Wednesday Night Skate crew we're going with (you should definitely feel confident enough on your skates to keep up). Best of all, it's free to all, just bring your own gear and a positive attitude, because whether you want to or not, you're gonna make some new friends. Get updates and more information on their Facebook page.