Most Vermonters put snow tires on their car before late December and a snowstorm can easily add travel time (several hours is unlikely but possible). A local will wait until the snowstorm stops and the roads are cleared but a visitor will often plow on to their destination in the worst driving conditions. Having skidded off the interstate once in a similar scenario (I-79 in PA), I recommend snowtires and anticipation of extra travel time. Snow driving experience/abilities is another factor to consider.

IMO Woodstock is probably nicer and more interesting for the first time visitor.