u/AtariFerrariNH

Especially ones that work HPN or north?

I'm starting to fly in and out of LDJ a fair amount, and I know the complexities of getting in and out of there IFR. I also know its nearly impossible to get an IFR clearance airborne in N90's airspace. But what about north of HPN? It is easy to get out of LDJ and northbound on the river if it is lets say 2000 OVC, but I wouldn't be able to get to my destination in the BOS area VFR. If I get up near POU, is there any chance at all I'd be able to get an airborne pickup?

Thanks in advance.