I rode up and over Beartown Mountain, including about 5 miles unpaved. The gravel roads were in good condition, and they were cris-crossed with hiking paths through the state forest. The torrents the night before created lots of nice water hazards, including a spot where I had to hoof it through a flooded it almost up my knees.
I re-joined the paved road near Monterey, then rode up through Tyringham and back. The last bit was wonderfully scenic, highlighted by Santarella, a bizarre gingerbready house.
Our visit to the Berkshires was spectacular, and the cycling certainly added a lot to it - we'll definitely be back later this summer.