Originally Posted by Pobble.808

What is your starting point? Hand Hollow? Do you want to walk out the door, jump on your bike and go, or are you willing to drive to a different starting point?

In a general way, I'd say that the area north and east of your previous loop, starting around Dalton and Hinsdale, should be pretty nice, probably a little bit hillier too but not killer. Personally I'd avoid Lenox and Stockbridge even more than Pittsfield -- narrow roads and too many cars, especially in the summer.