I'm trying to put together a compiled list of favorite skating routes. I'm starting with NYC because it's my hometown and current place of residence, though ultimately I think everyone should be able to include their personal favorites. I think the best way to do this is with input from people in this community. So if anyone has recommendations, please volunteer them!
My top favorite route to skate is going to have to be Riverside. Basically from around 121st street on the westernmost side of Manhattan, to down around 18th st. It's a super beautiful, scenic ride. Especially if you go on a nice day around sunset, you get a preposterously pretty vantage. I'm hoping to shoot some video of me skating exactly that sometime soon.