A big part of Cumberland Gap’s history lies in the story of famed American pioneer and frontiersman, Daniel Boone. His expedition through the physical mountain pass of Cumberland Gap helped ignite the fire of expansion to western territories beyond the borders of the Thirteen Colonies, first by the exploration and settlement of Kentucky.
Boone and his team of approximately 30 men were hired in 1775 by the Transylvania Company to blaze a more passable trail from Martin’s Station in Rose Hill, Virginia through the Cumberland Gap. By the 1790s, that trail had been cleared and widened enough by Boone and his team to make passage possible for wagon traffic. That path was called Wilderness Road and eventually earned the distinction of “Gateway to the West.”
This unique history can be felt in and around the town of Cumberland Gap, and it’s a source of pride for many who call this place home. That’s precisely why the town erected a monument to commemorate Boone and his adventures. This stone monument is next to the Cumberland Gap Town Hall, located at 330 Colwyn St.