AaronK wrote:
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.

No reason you can't do that here. File to Bridgeport. NY Tracon runs
both BDR and ISP; once you get into NY territory, getting a reroute
should be pretty simple (and will probably just be vectors). Stay
away from DXR and HPN, that's a really busy sector and unusual
requests may be harder to accomodate. A route that takes you over
Kingston or Pawling VOR (or anything north of that) will keep you in
airspace where the controller is probably pretty bored most of the
time.