So I've now ran this race twice - once two years ago (the 5K) and last week the 10K. I love NYC Runs because they always provide an awesome race experience.
Roosevelt Island is a random island that really isn't part of any of the 5 boroughs physically. It's a small island in between Manhattan and Queens and running around it is about 4 miles.
Packet pick up was done at JackRabbit Sports the Friday before the race but I ended up picking up just that morning. Because the 5k started at 9:30am and the 10K at 10am, my sister and I rolled in after 9:30am. We picked up our bibs and race swag (a large mug with a mini logo of the race). The mugs looked like the company screwed up - the logo was really small. Two years ago they had these amazing large green mugs that I still use to this day.
Had I known that they don't start the race until every 5K runner finishes, I would have slept in for another half hour. The 10K didn't start until 10:20am. At that point, I was freezing. It was around 30 degrees when we started. The course consists of two laps the island. The start and finish were right by the tram station and because there was construction of the lower southern half of the island they changed the course just days before the race.
The island isn't much to look at although the mini lighthouse at mile 1-2/4-5 is cute. What is awesome is the views of the Manhattan skyline and the river along all sides of the island. The Queens side of the island is all industrial and not pretty to look at.
I think I counted 2 water stops along the race (or really four because of the 2 loops). My highlight of this race is that one it's cheaper than NYRR races by a lot and the food is better. I paid $30 for the race but I could have paid a lot less if I signed up 2 months ago. The bagel spread is amazing and from Terrace Bagels (real authentic NYC bagels unlike the stuff NYRR gets), lots of fruit to grab like grapes and apples and the hot chocolate was AMAZING. For the bagels, they had the standard cream cheeses and butters.
Overall, it's a holiday favorite with great food. NYC Runs hosts different "hot chocolate runs" in different areas of the city during the winter including Brooklyn and Riverside Park. But because this one is so close to the holidays, it's probably the most festive one (I wore my crazy Christmas compression socks).