I spend about 4-5mo/yr in the Berkshires ( This shot is technically East of Berkshire county). The roads are absolutely incredible. I have 3 high performance cars, but the roads are so good they're just nice to drive on and take in the scenery. No need to hammer it, because you'll miss something beautiful. Riding would be even more incredible because these roads are never crowded and are curvy. Just watch out for the leaves...

And your GPS will crap out in various spots, but I know the area well enough it's not a concern for me. And some roads will suddenly just turn into gravel. If you're not familiar with the area preload the maps, save them, or print paper copies. Trust me, you'll need them if you're not familiar with with the area.