Stockbridge, Pittsfield & the Narrow Valley — a stop on Vermont Route 100.
Through Stockbridge and Pittsfield now, and the valley tightens right up — the hills come in close on both sides and there's barely room for the road, the river and a strip of field.
That geometry is exactly why this stretch suffered so badly in Irene, and in the great flood of nineteen twenty-seven before it. There is nowhere for high water to spread out, so it goes UP, and it takes whatever is in the valley bottom — which is the road you're driving on.
Pittsfield is tiny and has a pretty village green, and it has a slightly unlikely modern claim to fame: it's become a hub for extreme endurance racing, the sort of events where people run up and down these mountains for days. On a summer weekend you may pass some very tired-looking people.
You'll also start seeing more ski traffic through here — we're getting close to Killington, and the condominiums and rental places begin to appear.
Keep an eye on the roadside for farm stands. Maple syrup, cider in autumn, eggs on the honor system with a coffee can for the money. That last one is very Vermont, and it works.