I’ve been following a guy named Mark Ervin who started paddling the “Greater Loop” 3 months ago from Nova Scotia and went up the St Lawrence to the Great Lakes. He posts a video a week or so and puts them out in near real time. In the next video or one after, he should reach Chicago, from where he can start downstream to the Gulf. After he reaches there, he turns left and paddles along the coast to Nova Scotia.
Rock formations are mind boggling to me living on Long Island a giant sand bar. Never look up at anything on the south shore. Few small cliffs on the north shore but no rocks.
This is a good chronicle of a guy and his dog paddling a canoe starting near Toronto up to Geogian Bay. One episode he crosses from the Bustard Islands to Lonely Island (about 30 miles in 9 hours). Worth watching: