Williams is hillier, near the top of the Berkshires. Anything you ride there will be hilly. Amherst is pretty flat, but only 10 miles from the eastern slope of the Berkshires. Amherst to Wilmington, VT is a little over 50 miles, via Conway, Shelburne Falls, Colrain, Jacksonville, and a beautiful ride to boot. From Williams, you're right at the crossroads of the Berkshires, the Taconics, and the Green Mountains. Both have their pros, and not many cons. Enjoy! Oh yeah, it snows in the winter. Learn to ski (XC or downhill), snowboard, or snowshoe.