My mom lives in Charlemont. Right on the Deerfield River. I'm over that way on occasion. I'll drop you a line over the summer, maybe go for a cruise. Route 2 is a pretty fun drive. Taconic Trail park section and the wicked hairpin after North Adams!!! SCREEEEEE!!!!! hahahahah.
I mostly stick to western/central NY. The NE is a dead zone for car stuff I feel like.