I usually don't go a huge distance upstream, but just for time reference, last year I put in @ Harlinsdale & paddled upstream to Pinkerton & it took about an hour I think. I had to portage 6-8 times.
I started wearing waders/boots & connecting a shock cord (kayak to waders) & portaging became a lot easier on Harpeth for me. Especially when fly fishing...I connect & drag it behind me. Have less issues w/ line / trees / anchoring etc
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