I looked at your blog, Suze. We usually do a trip to the Berkshires every year; next one may be the weekend of the 22nd, depending on the weather.
I've done many of the routes you described. It was fun to read someone else's descriptions.
I have to say riding in the Berkshires is almost as tough as riding in Europe. Last year, I did the climb up Monterrey Rd, as opposed to the Tyringham "wall." I almost didn't make it, but I did, at times seeing 3 mph on my computer.
Alford is one of my favorite towns. Did you know you can use the rest room at the town hall, without asking? It's always open.