The New York City Inline Skating Guide
Where to Skate: East River Islands
The combination of walkways and road make the perimeter of Roosevelt Island a fairly pleasant skate, especially during the summer when you can catch a breeze off the East River. The entire route is about four miles and almost entirely flat, so you can do it in a very leisurely hour. In general, this "trail" is in good shape, although the sidewalks are often brick or wood rather than concrete or asphalt. On the east side of the island, by the bridge to Queens, there is a set of steps of just about the right number and steepness for stair newbies to practice bashing. You'll probably run into some neighborhood kids doing just that.
The main problem with skating Roosevelt Island is that there is a security service patrolling the island, and they seem to like to crack the whip. It's not uncommon to have one of them sneak up behind you and then use the PA system in his truck to announce that you're supposed to skate in single file along the side of the road. They'll really give you a hard time if they catch you skating the ramps in one of the parking garages.
There are two routes on/off the island. The tram from Manhattan starts at the corner of 59th St. and Second Ave. and costs $1.50 (or a subway token) each way. The tram people are pretty cool about skaters, so you won't have to remove your skates in order to ride the tram. There is also a bridge from 36th Ave. in Long Island City, Queens, which connects with the second level of a parking garage about 2/3 of the way up Roosevelt Island. To get to the bridge, you have to go up an escalator or elevator inside the garage (just look for a Sloan's grocery store; the escalator is right next to it). The walkway on the bridge is skateable, although it's a bit bumpy at each end.
The Queensboro Bridge from Manhattan to Queens passes over Roosevelt Island but offers no access to the island.
Even seasoned New Yorkers go blank when you mention Wards Island and/or Randalls Island to them. The confusion is soon cleared up when you say that it's the island (singular; what were two islands is now one) above which the three arms of the Triborough Bridge come together. But know the name or not, there is some pleasant skating here.
To reach the island(s) by skate, you have two choices, the walkways along the Triborough Bridge to Manhattan, the Bronx and Queens, or the pedestrian bridge which connects to 103rd St. in Manhattan . Problems to contend with on the bridges include occasional garbage and puddles on the Triborough walkways and unpredictable closure. The Triborough walkways can be gated shut (though not necessarily all at the same time), and the middle section of the 103rd St. bridge is sometimes lifted to let boats pass under and then left up for extended periods.
In a sense, Wards/Randalls Island is a big park with a few large facilities plopped just south of the halfway point, including the Manhattan Psychiatric Center, a wastewater plant, and a firemen's training school. Occupying the north half of the island is Randalls Island Park; curving around the south edge is Wards Island Park. The lanes in both are open to cars, but that's because both contain a number of baseball fields, picnic tables, etc. You will encounter some traffic in Randalls Island Park, but Wards Island Park is much quieter.
Besides the traffic issue, Wards Island Park is a more pleasant skate than Randalls Island Park anyway. True, it's much smaller, but the lanes are generally in better condition, there are more trees giving you shade and reducing the wind, and there's perhaps a more scenic view. There's also a bit more variation in the terrain. Nevertheless, neither park will be a challenge to skaters looking for distance. I'd recommend Wards Island Park as more of a place for newbie skaters looking for a quiet, out-of-the-way place to do some learning, or for just having a picnic.