US20 from pittsfield to Albany. Also Hwy 8 to North Adams, Mass.
I had this run a couple times in the semi, although I hate the run being super heavy, i think it would be quite a blast in a car. I start in N Adams and come down 8 which is a twisty windy road that is pretty scenic lots of hills, then you get on 9 to go west thru pittsfield then west on US20 to shortcut to the tollway in albany. From pittsfield to albany your constantly shifting from all the elevation changes and tight switchbacks.
If your going from Albany area to Northern/ Northeastern Mass and have some time to spare, I highly suggest this scenic route.
US20 to pittsfield, 9 to 8 north, then 2 east to US202. Its been a while since I did this run so im sure Im missing a lot of cool things about this route, but I do remember that on my way to N adams empty I had a blast.