I first went through the Delaware Water Gap, then along US 6, then up the Taconic State Parkway, then NY 55, then up US 7, detouring over 41 between Great Barrington and Pittsfield. Allmost all very scenic despite the relative proximity of New York City. The final part was were the rich live: full of nice houses, but also lots of quaint churches.
Pictures (click for larger size):
