One of the first pioneers to cross the Appalachians mountains into Kentucky

   When europeans first came to America they setteld between the Atlantic coast and the Appalachian Mountains because they were difficult to cross. The goverment did not allow colonist to pass this mountains because the other side was indian territory. This rule was doing fine untill the land at the east of the Appalachian started to fill with farms and towns built by the colonists. They wanted more to fulfill the people´s needs. By the late 1700s many settlers crossed the Appalachian. But it was Daniel Boom in 1769 who discovered an indian trail throught the Cumberland Gap, he helped built there a road with the name of wilderness road.  

  But many years before that there was a group of people that tried to cross the Appalachian Mountains, the first european explorers were from Spain, Hernando de Soto and his troops traversed the region in the 1540 searching for gold. The first english exploration of the mountain were from a guy named Abraham Wood which began around 1650, he sent exploring parties to make direct contact with the Cherokee tribe in order to stablish a trade relationship.

  Althought there were many explorations before the Boom´s one, Daniel was the first in create a trail known as the Wilderness Road, it was steep, narrow, rough and could only be traversed on foot or horseback, despite this many people used it particularly slaveholders after some states had abolish the slavery and become free states.

I hope that the answer help you.