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What I know about follows. There may be other obstacles farther east that I'm not aware of. The Friends of the Winooski River is probably a good source of information, since they have run multi-day canoe and kayak trips from Marshfield down to Lake Champlain, and are concerned with the entire Winooski River watershed.
Near the crest of the hill that descends down into E. Montpelier there is an old low-head dam with a fairly nasty hydraulic below it, plus possible wood hazards. It can be portaged on river left. There is a large turnout on Route 2 opposite the river side, about 100 yards downstream of that dam.
The pool below the dam leads into a class 2/2+ rapid that covers a few hundred yards. After that is a flatwater section that ends at the next dam, which is a full power generation dam, referred to (I think) as the Montpelier No. 5 dam (from this report). Informally it is known as the Kubota dam, since it is behind the Kubota equipment dealership on Route 2 in East Montpelier. It can be portaged on river right.
Below that dam is about 1.5 (?) miles of class 2/3 whitewater running down to and beyond Route 2. The harder stuff is up near the dam. The Fiddlehead Slalom (May 14, 2017) is run below that. There is a trail along the river that is used during the event, as well as by fisherman.