Perry – I paddled the Connecticut from Canaan to the Wilder Dam two years ago. There are no ‘bad’ sections in that 140+ miles, but from Canaan to below Maidstone is probably the stretch that gives you the most sense of being surrounded by forests and mountains. From the Comerford Reservoir to Wells River is also quite pretty, as I recall. And I was fascinated by the Connecticut River hydroelectric dams, and i am glad to have seen and portaged them.
My favorite campsite was Lyman Falls, probably the least-known state park in Vermont, basically a couple of primitive sites by the river. I made my trip the first week in July and barely saw another paddler the whole time. Fall is a great time for canoe tripping in the northeast, as you may know. No bugs, no crowds, and the water levels begin rebounding from summer lows.
If you send me your email by private message I will send you our trip report including notes on water levels and portages. – K