Every summer I bike from Wassaic NY to Lenox MA, then back from Lenox to Poughkeepsie. The route is due to the fact that my sister works in Lenox in the summer and the Metro North train has it's northern most stops in Wassaic and Poughkeepsie.

In any case, there's lots of great riding up there. Some nice rails to trails, but for the most part I just study google maps and pick quiet roads. I've done it 5 years in a row and managed to go a completely different way each time. Using a combination of topographical view, satellite, and street view you can get a good sense of what you're riding on. The whole area of Taconics - north western CT, western MA, and NY east of the Hudson in gorgeous.

If you're interested in the area let me know, I've covered a lot of ground there and could recommend sights to check out or which roads are the nicest. I don't check this forum too often but you can reach me at sm1ff1cus@gma1l.com (convert the 1's into i's).