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.