Originally Posted by
7speed
I'd say Deerfield, MA.
For dirt roads, I'd use as much of the
D2R2 routes as possible. I'm sure there is nice road riding on the paved rural roads of that area. For the canoe, I'm sure there's something around that fits the bill, perhaps the Green River or the Connecticut.
Dang! I read the OP and before I scrolled down to see your post I thought "Deerfied" for the reasons you mention. I did the 100K route of D2R2 in '12. Beautiful course. I am was a four-year "Deerfield Boy", class of '83, back when there were no girls. Hadn't been back to the campus since '91.
The Deerfield River runs along the west end of the town, and the CT River is not that far of a drive.