Fall 2000, KenR:
Greg, Tony, Sharon, and Ken drove up to Hancock on a perfect sunny day and started out around 9:15. Little traffic climbing up, and great views from the summit of Mt Greylock. But more potholes on the way down than last year -- and it's not a real fun descent on a tandem, since a tandem is so fast going down, and you have to do so much braking. We tried out the Old Cheshire Rd descent (instead of the Quarry Rd dirt shortcut) and that was good. The cruising down to Williamstown was fun. But the last section on Rt 43 South from Rt 7 was into a headwind, which made the uphills feel a lot tougher than on previous trips.
A fine day, well worth the trip, but now that we've ridden up to the Mt Greylock summit twice and seen the views, next time we might skip the big climb, and do some additional exploration down below.
Story of this route
Ken's story: I don't remember the details, but sometime in the 1990s I learned that it was possible to ride a bicycle to the top of the highest mountain in Massachusetts. But it was so far for us to get there from the south, that we wanted to add some more riding, to make it worth all that driving -- and find a start point near NY Rt 22 to make it less driving. And Tony had a friend in Williamstown that we wanted to try to visit. So that led to the idea of going around Mt Greylock.
Then we just took our best guess at what would be some quiet roads, and as we rode it we found that we liked most of our guesses. So we got most of the route the first time, then refined some things in further visits.
We've made a couple of tries at extending the loop further north or further south, but haven't found anything good enough to be worth adding as a longer option.