You could go up the Allegany to the Connowango up it to the cassadega to the Chadiquoin up that into Chitauqua lake and then do the ancient carry into lake Erie,then a short way to Buffalo and then the Erie canal to the Hudson.
I an only faniliar with the Commowango-Chitauqua section and have paddled some or the Erie canal.
Full Size Sail Rig
Kayak & Canoe Covers
Electric Kayak Motor
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