getting to Long Island (KISP) IFR from Michigan

AaronK wrote:

I'm wondering what kind of routing I'm likely to get around NYC. Coming
from Michigan I have a choice of Canada to Buffalo and down, or to Toledo
Ohio and then east. A friend said I should file to Pawling VOR, then
basically the LOVES2 arrival route, because I will likely get that anyway.

The two times I flew from Buffalo, NY, to Farmingdale airport on the island
that route was more or less the route I received. Pawling, then over
Connecticut near Bridgeport and south over the Long Island Sound.

But when I do a Duats or Aeroplanner low altitude auto-route I get:

Starting from Toledo (KTOL) I get a route around south of Manhattan (SBJ,
EMPYR, NANCY, PROUD, JFK, DPK KISP)

You can certainly try to file this. Coming from Islip back to upstate NY
one time I received direct JFK, then northwest over Manhattan and on up.
It was a very scenic flight, as the sun was down and it was evening rush
hour down below.

1. anyone have experience at various altitudes (under FL120) from the west
to KISP area?

NY will most likely begin bringing you down from whatever altitude at which
you are cruising to around 4,000 feet or lower after Pawling. This can be
a problem for you, however, given the fact that you will be crossing the
Long Island Sound. I have requested to remain as high as ATC could allow
while crossing, using the excuse that I am a single engine without
flotation gear. Both times I did this I was allowed to remain at 5,000
until reaching Long Island.

2. can you get flight following and get to ISP VFR? What would be the best
route and altitude for that? (with no ice protection, I might need VFR for
altitude at my own discretion)

Sure you could. If you stay to the north and out of class B airspace, you
should be able to cruise at an altitude of your choosing. What altitude?
The higher the better when crossing the Sound, IMO.

Be extra vigilant when scanning for traffic (VFR or in VMC when IFR), as
there are a lot of airplanes over a relatively small area near NY. Don't
be comforted by being IFR. I have personally encountered an aircraft
crossing just below me when approaching Teterboro that apparently didn't
have his transponder on (no traffic call by ATC and it did not appear on my
TIS). My aviation mentor told me a similar story when he was flying an
MU-2 on approach into Teterboro.

--
Peter