I'd head over to Pittsburgh, where you can connect with a bicycle trail system that heads down from there to Cumberland Gap, and from there all the way to Washington, DC. I'm told you can go from Pittsburgh to DC without riding on a road.

From there, you can cut over to Delaware, take the Lewes-Cape May Ferry up to Cape May, NJ, and then ride up the New Jersey coast, catching a ferry to NYC.

This would add total distance perhaps, but make for a lot of scenic and relatively flat riding.

Tailwinds to ya!