GT
I think that is about right on the time.
The Berkshires are about 3 hrs from me, NYC and LI are 4-5ish depending on traffic.
The ferry from LI (Jeffsport ?) is a quick shot around the city and 91 will take you right up to springfield, MA and the mass pike otherwise I would think it would be a nice ride up through the poconos.
mapquest.com
mabblast.com