Possibly riding to St. Johns NF by way of Canada.
...you do understand there is a 6 hour ferry ride to NF at Port Aux Basques then 900 km to St. Johns.....or 14 hours plus 130 km via Argentia
Welcome to Newfoundland :: Getting there
Then you have to do the return.
How much time do you have ??
This time question actually applies to the OP as well.
Son and I opted to fly our bikes from Toronto to Vancouver to cut out the arduous against the prevailing wind trip going west. ( it should be available again this year ..cost us $700 each )
Bike on the plane, no special prep other than 1/3 gas full. Get to Van, 5 minute taxi to Air Cargo ..we arrived 10 am,,,on the bikes by 11 and a wonderful first day riding up Sea and Sky and 99.
With that - 3 weeks was a comfortable trip time then giving us a good run in BC north to just touch Alaska at Hyder/Steward ( not to be missed )
We skipped Banff and Jasper tho could have used a spare day we charted out for Jasper,...instead it was needed for a rain day
Then across to Vancouver Island for a few days, Port Alberni etc ( what hoot that highway is ) Then ferry across from Nanaimo, then through Vancouver and along the border via The Crow's nest pass to Glacier National Park ( excellent but be prepared for wild weather )
Then Yellowstone ( mind the bison ...seriously..mind the bison), the Beartooth ( must do ) ...the Chief Josephs and slabbed home via South Dakota which was gorgeous in spring and very fast HWY speeds - 85 mph plus.
Chicago traffic sucked but slid through with good timing and stayed on the eastern edge , then home the next day 22 out of the 24 we allocated.