20+ years ago, I was on a delivery of a 56' Ketch from Antigula to Chicago. And as I recall we stepped shortly out of NY up the Hudson. Went to the Erie and didn't restep till we hit Rochester, headed across to Toronto and back to the states via the Welland. Lots and Lots and Lots of MOTORING; once we hit NY. I haven't looked at the charts for the Illiana Canal or the Mississippi. Lake Champlain is sailable, the Great Lakes definitly; but in the Hudson, Canals, Illinois and Mississippi plan on motoring. Upper NY state and the Hudson are absolutely beautiful, plan on stopping at West Point for a tour and if the Irish Pub is still there across the river, good place to get a good Guinness. Also, when passing through Ilion, visit the Remington Arms Factory; it is amazing. And another stop in Rochester, if you like Cheese Cake, I don't remember the name; best Cheese Cake I have ever had. Some where in my cellar I have the log of the trip... DAMN.
Nik