six years ago i registered a cr250 in VT. I live in MA. did it through the mail. 250cc and less are not required to have insurance or inspection. had to send a copy of the bill of sale and pay sales tax (I think?). don't know if they closed that loophole yet. but it was very common to have VT plated bikes at turkey runs and enduros. for short dollars you could give it a try and see how the locals react.
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MC21R9N track
MC18R2J track
CBR954
CR250