Thanks for all the good advice everyone. Flightaware.com is great! Didn't
know about that one.

I really don't want to get vectors out over the water south of NYC. Maybe
the Buffalo route is more likely to get some kind of routing over the sound.

One trick I've used to help avoid over water routing around the great lakes
is this. I file two flight plans, the first being to a destination that
gets me past the lakes, then when I get close to my first destination, I
pick up my second clearance in the air and continue. This gets me a
gauranteed L shaped flight plan.

But with icing, lots of traffic/ATC and over water possibilities, NYC area
is a bit dawnting. I think if I shoot for good VFR conditons in the NYC
area, I'll have more options open.

One more question, are there a few "gates" approaching NYC are that I should
be farminiar with? ... Aaron