This charming Revolutionary War-era town has plenty of wintery fun in store. Visit one or all of the three nearby ski areas, ice skate on Bantam Lake or head to White Memorial Conservation Center, which has 4,000 acres with 35 miles of trails for snowshoeing and cross-country skiing. After checking in to the odd yet wonderful hotel at Winvian Farm, warm up by sampling Connecticut-made whiskey and gin at the Litchfield Distillery or catching a movie at Bantam Cinema, the state's oldest continuously operating movie house.