Get a trail map from VAST, I have one and they are great... but I will say even with a map the numbering system in VT is confusing in places. Last time I rode there I got all mixed up.
It'd be a pretty ride - no doubt a full day, maybe more to get there.
Yes VT does require insurance so have proof of it with you and there is a state wide speed limit just as there is in NH.
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