This is not a hiking trip, but for Canadian adventures, I know a person who took this unbelievable trip:
He drove 400 miles from Boston to Goose Bay, Labrador. From there he took the ferry two days (about 400 miles) north to Naim (the end of the line). From there he paddled his sea Kayak to the northern tip of Labrador through the fjords of the Tongat mountains (about 400 miles), through the McLelan Strait (which has the world's strongest tidal currents), and then down the east coast of Quebec (150 miles) to the air strip at Kangiqsujuaq from where he could fly home (but he had to leave his kayak behind as it wouldn't fit on the plane). And when not doing adventures like this, he won the Nobel Prize for Chemistry. Boy do I feel like an under achiever.