The Wilderness Road was started by Daniel Boone. He led people through the Cumberland Gap. The Wilderness Road had two parts, one in Virginia and the other in Kentucky. In between, the traveled in Tennessee. The Wilderness Road started around the 1770s. There were over 200,000 settlers who traveled the Wilderness Road. People traveled on the Wilderness Road looking for new land to settle.The place where these people lived were getting crowded, so they want to be new pioneers in a new place. 

Here is a Goggle Earth Map that shows the Wilderness Road.  

This is a painting of Daniel Boone leading settlers through the Cumberland Gap. The painting is by George Bingham, and is titled “Daniel Boone Escorting Settlers Through the Cumberland Gap”*