I've never ridden anything like that but I do live in CT and if I were you I'd try to go south early, perhaps in RI and consider doing some extra miles to avoid the hills of northern CT. Although if you stay north you will avoid a lot more urban areas. There's a ridge in central CT plus tons of rollers in eastern CT, but it's probably better than the birkshires.
Also, I'm not sure if you meant in one day or not, but if it's not in one day just go for the most rural/safe route. Hills are part of life, you just don't want them to kill you on a long day.