First hurdle will be getting a boarding pass because unless you have a B1/B2 visa or something equivalent, they will not let you on the plane unless you are a very fast talker. The airlines know they will be out of pocket if you get denied entry on landing so they have a vested interest in making sure it doesn't happen
If you intend going flying in under the 90 day visa waiver system and driving out at a land border, they do have a system to allow that but it supposedly requires setting up before you arrive.
If you are taking your bike in to the US then the paperwork might be accepted as proof of onwards travel. We left a vehicle in South America for several months a couple of times and we were stopped from boarding at the last point in the EU until I showed the checkin clerk the TVIP and vehicle registration papers
The other thing you will need to do is to check on how the US visa stay clock works because they usually count short visits into Canada and Mexico as adding to the time allowed in the US so if you land in the US and spend 80 days there and then cross into Canada for 20 days you run a real risk of not being allowed into Alaska or mainland US. If you spent say 70 days in Canada that might be viewed differently.
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