If you are starting from New York City, you'll probably ride across the George Washington Bridge... and then?

Here's a website where you might get some clues:

http://www.crazyguyonabike.com/doc/l...octype=journal

Mostly you'll be riding through the big white spaces on the map. The biggest challenge riding is probably avoiding narrow roads with too much traffic. Monster hills aren't much fun either!

Sounds like a great trip!