I haven’t done it, and I think it would be a nice trip, however, I think its been done so much that I would want something more unique.
I knew a guy who started at the Statue of liberty and kayaked to the Pacific ocean, portaging over the great Divide. I still have his trip notes and wish I could find him again to see what happened to him (it was 1992).
The journalist Eric Severied canoed the Red River in N. Dakota north to Hudson’s Bay in 1932.
Those sound like Awesome trips!