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Daniel Boone and the Wilderness Road: Kentucky History

Updated: Nov 22, 2020

I've always heard about Daniel Boone and how he was this amazing and legendary frontiersman and folk hero, but before today, I couldn't recall even one of his accomplishments off the top of my head. So today we're going to learn about Daniel Boone and the Wilderness Road!

Daniel Boone was a pioneer, explorer, soldier, businessman, and politician most famous for his exploration and settlement of Kentucky. Born in November of 1734 in Reading, Pennsylvania to his Quaker parents who were fleeing religious persecution in England, he was the sixth of eleven children. Growing up at the edge of the frontier, he received his first rifle at the age of 12 and began to learn hunting and trapping skills from both local settlers as well as hunters from the nearby native Lenape tribe.

As a young adult, Boone made a living by hunting game and selling fur at the market as well as maintaining his own farm. Through this work he begun to familiarize himself with routes through the wilderness, which would help him when it came time to blaze the beginnings of the Wilderness Road in 1775.

The Transylvania Company commissioned Daniel Boone to create a trail from Fort Chiswell, Virginia through the Cumberland Gap in 1775. The Transylvania Company chose Boone because he was considered to be the most experienced and knowledgeable explorer of the area at the time. The company's goal was colonize the resource-rich area and establish "Kentucky" as the 14th official colony.

Native Americans such as the Cherokee already used these lands for living and hunting. To avoid aggression from the Native Americans, who had already attacked Daniel Boone's group of settlers in 1773, killing multiple people including one of his sons, the head of the Transylvania Company attempted to negotiate with the Cherokee directly. A compromise was eventually reached; the Cherokee agreeing to sell the land in exchange for 10,000lbs of goods. Predictably, the goods were never received as the colonel governor of Virginia later nullified the sale.

In March of 1775, Daniel Boone led a group of around thirty men to begin the journey through the wilderness. Using axes, they began in present-day Kingsport, Tennessee, and started trailblazing north. Early traces of paths and trails used by buffalo as well as native American warriors were used to help create the road.

After getting through the Clinch Mountains, the party crossed Clinch river near present-day Speers Ferry, Virginia, following Stock Creek until they were able to cross through Kane's Gap into the Powell River Valley. Soon before reaching their desired location for the new settlement on the Kentucky River, the group was attacked by Shawnee tribe members, who had not conceded their rights to the land. Most of the group managed to escape, but there were some fatalities. Soon after, the group finally arrived southside of the Kentucky River in what is now Madison County, Kentucky in April.

Wilderness Road was more than 200 miles, starting in Virginia making it's way through multiple mountain ranges and into central Kentucky, allowing the foundation of the first settlements such as Boonsboro, Benjamin Logan's, and Harrod Town. At first, the road was steep and rough, the only way through being horseback or on foot. However, the rough terrain was not the only obstacle travelers faced. Outlaws would often ambush small groups in order to rob and loot anything of value. Native Americans from tribes such as Chickamauga and Shawnee, who no agreements had been reached with, would also organize attacks against settlers encroaching their ancestral hunting grounds. Dangerous wildlife such as bears, panthers, and wolves as well as venomous snakes and insects posed a threat too.

Despite the danger, Wilderness Road was used by hundreds of thousands of people. Eventually, using Native American trails, the road was lengthened all the way up through Louisville, Kentucky ending at the Falls of the Ohio. The trail was also widened and re-routed in some areas to allow the passage of wagons and carriages.

It's estimated that as many as 300,000 settlers traveled along Wilderness Road from 1775 to 1810. The route was also used by farmers and merchants to sell their goods at markets closer to the coast as well as supplying much needed food and items to new and growing settlements in Kentucky.

Use of the Wilderness Road had declined by 1840. The progression of steamboats, ferries, and waterway travel through the Eerie Canal as well as the opening of the National Road led to the eventual decline of travelers. A segment of Wilderness Road was one of the first roads to be paved in the United States. The trail would also be linked to Dixie Highway, connecting Detroit, Michigan to Miami, Florida. This led to a boom in tourism and industry with many restaurants and hotels appearing along the route. There are many historical sites along Wilderness Road that you can still visit today!


Westward Expansion: Wilderness Road - - April 2010

KY Wilderness Road - - December 2019

Daneil Boone Wilderness Trail - - 2015


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