Portal:Kentucky/Selected article/9

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The Wilderness Road was the principal route used by settlers to reach Kentucky for more than fifty years. In 1775, Daniel Boone blazed a trail for the Transylvania Company from Fort Chiswell in Virginia through the Cumberland Gap into central Kentucky. It was later lengthened, following Native American trails, to reach the Falls of the Ohio at Louisville. The Wilderness Road was steep and rough, and could only be traversed on foot or horseback. Despite the adverse conditions, thousands of people used it. In 1792, the new Kentucky legislature provided money to upgrade the road. In 1796, an improved all-weather road was opened for wagon and carriage travel. The road was abandoned around 1840, although modern highways follow much of its route.

Because of the threat of Native American attacks, the road was so dangerous that most pioneers traveled well armed. Robbers and criminals also could be found on the road, ready to pounce on weaker pioneers. Although the Transylvania Company had purchased the region from the Cherokee, and the Iroquois had ceded it at the Treaty of Fort Stanwix, other tribes, such as the Shawnee, still claimed it and lived there.

During the American Civil War, both the Union Army and the Confederate States Army used the Road. An early battle (Camp Wildcat), stymied the first attempt by the Confederates to seize control of neutral Kentucky. The Cumberland Gap changed hands four times throughout the war. The southern armies used the road for marches into Virginia. General Ulysses S. Grant came down the road for the Union campaign in Tennessee in 1864. Grant was so taken by the Road that he said, "With two brigades of the Army of the Cumberland I could hold that pass against the army which Napoleon led to Moscow."