4. Route 100, Vermont
Ski Areas: Mt. Snow, Okemo, Killington, Sugarbush, Stowe, and nearly every other Vermont ski resort
Road Conditions: http://511.vermont.gov/main.jsf
This is one of the highways I grew up skiing. It cuts down the center of Vermont, roughly paralleling the Green Mountains to the west and passing by more than a dozen ski mountains on its way.