Whiteface Mountain Resort, New York
Simply put, the best challenging terrain on the east. Can drive from NY. The nostolgic olympic village has great food, cheap lodging, good nightlife, and plenty of activities off the mountain. Perfect in winter or summer. Village is always filled with nice people Local & tourist)ready to spark up a conversation.
It's a former Olympic mountain with great trails and beautiful scenery. It's also close enough to drive to for the family.