In 1775 Daniel Boone and a group of axmen, following a Native American trade route, blazed a trail from the Anderson Blockhouse to a site on the Kentucky River. This trail, later called the Wilderness Road, crossed 200 miles of wilderness and met several natural barriers, including the Clinch River. In the eighteenth century, the gorge near the crossing allowed passage only for Troublesome Creek, which earned its name from the difficulty it caused travelers trying to follow it through the gap to the river. The ford lay on a shelf of rock under the present bridge and, though usually safe, became dangerous in high water. In May 1779 a militia party escorting British Governor Henry Hamilton, captured at Vincennes by George Rogers Clark, nearly drowned while crossing here on the way to Williamsburg, Virginia.