Occasionally folks ask about the road conditions while traveling. I stumbled across a couple of Vermont web sites that might prove of interest: VT MAP Conditions explained
You bet it would. Designing a rally not in vermont at one locale, but as a "rally" on the move throughout vermont would be an expedition in itself on back roads (winches may be required) !
...places like enosberg falls, jay, smugglers notch, green mountain national forest, ripton, etc...
...setting something up like this would need heavy planning, a pre-run, etc...