The Wilderness Road — Daniel Boone’s Path into Kentucky


The Wilderness Road, which was blazed by Daniel Boone and a group of men under his command, was a vital route for American pioneers who emigrated west in the late 18th and early 19th centuries. It is believed as many as 300,000 people took the Wilderness Road into Kentucky.

Daniel Boone, First View of Kentucky, Painting, Ranney

Boone’s First View of Kentucky by William Tylee Ranney. Image Source: Thomas Gilcrease Institute of American History and Art.

Wilderness Road Summary

The Wilderness Road served as a principal route connecting the colonies on the East Coast to the interior lands of the Ohio River Basin. The road was a broad loop that began in Virginia near the Potomac River, stretched down the Shenandoah Valley to Staunton, and then to the Holston River, continuing to Long Island — present-day Kingsport, Tennessee. 

The southern base of the loop extended west to Cumberland Gap and finally swung northward to the falls of the Ohio at Louisville, Kentucky. The most well-known segment of the road ran from the Long Island of the Holston to the Bluegrass area of north-central Kentucky by way of Cumberland Gap. 

Before commercial and settler traffic, migrating herds of bison and Native American Indians used the route, which was known as the “Great Warrior’s Path.” The Indians used the path to travel to the rich hunting grounds of Kentucky and to carry out attacks during wartime. Kentucky was a dangerous region, and is often referred to as the “dark and bloody land.”

A handful of Americans known as Long Hunters used the pass before the legendary frontiersman Daniel Boone traveled through the mountains in 1769. Boone returned in 1775 to cut a road for Richard Henderson, who intended to establish a colony in the area.

Although Henderson’s venture failed, the Wilderness Road paved the way for hundreds of thousands of pioneers to cross the Appalachian Mountains, and settle in Kentucky. The Wilderness Road played a significant role in the Westward Expansion of the United States.

Daniel Boone, Cumberland Gap. Bingham
This painting by George Caleb Bingham depicts Daniel Boone escorting settlers through the Cumberland Gap. Image Source: Wikipedia.

Fact About the Route of the Wilderness Road

  • During the late 1700s, the Wilderness Road led to the settlement of Kentucky and contributed to Westward Expansion.
  • The length of the Wilderness Road was 200 miles.
  • The route of the Wilderness Road started in western Virginia, moved southward into Tennessee, and then north into Kentucky.
  • The Wilderness Road started at Long Island of the Holston River, near present-day Kingsport, Tennessee. 
  • The road forked after passing through the Cumberland Gap. 
  • The southern fork passed over the Cumberland Plateau to Nashville, Tennessee, following the Cumberland River. 
  • The northern fork of the Wilderness Road also forked into two paths. The eastern fork went into the Bluegrass Region of Kentucky to Boonesborough. The western fork went to the Falls of the Ohio, which is at present-day Louisville, Kentucky.
  • The Wilderness Road played an important role in America’s fulfillment of Manifest Destiny.

Wilderness Road History

The Wilderness Road to Kentucky was an important pioneer route in Colonial America. Early travelers on this road played a significant role in settling the American West and establishing Kentucky as the first state in the wilderness beyond the mountains.

When the British Colonies were established, settlements were built along the East Coast. Over time, Americans traveled and explored the western frontier. Men known as Long Hunters and Frontiersmen learned about roads and passes through the Appalachian Mountains from Native American Indians, including the Cumberland Gap.

The pathway through the mountains was referred to as “Athowominee” by Indians, which translates to “Path of the Armed Ones.” It was also known as the “Great Warpath” and the “Great Warrior’s Path.” It was used by many different tribes to travel into the region, either to hunt or to conduct raids on rival villages. 

Wilderness Road, High Bridge, Kentucky
This postcard illustration from 1907 depicts the Old Wilderness Road at High Bridge, Kentucky. Image Source: New York Public Library Digital Collections.

Exploration of Kentucky Carves the Route for the Wilderness Road

For more than 200 years before the American Revolutionary War, explorers and hunters had been making their way down the Ohio River, touching the borders of what would become the state of Kentucky.

Early exploration by Europeans helped carve the path that was eventually used by Daniel Boone to blaze the Wilderness Road in the southern region of the Appalachian Mountains. 

Among the first Europeans to explore the region was Hernando de Soto, who led an expedition into the region. De Soto traversed the area from 1540 to 1541, in search of gold, which was never found.

Abraham Wood Follows the Great Warriors’ Path

The first recorded expeditions into the region were made by Abraham Wood, a Fur Trader, merchant, and politician from Virginia. Wood apparently made his way into the southern Appalachian Mountains in 1650, on the western boundary between Virginia and Indian territory. Wood traveled east on the Great Warriors’ Path with Edward Bland.

After he returned to Virginia, Wood sent follow-up expeditions into the area. In 1671, the Batts-Fallam Expedition made its way to the New River Valley and New River, which is part of the Ohio River Watershed. The expedition was led by Thomas Batts, and Robert Fallam, and included Abraham Wood’s son, Thomas.

In 1673, Wood sent another expedition into present-day Tennessee to trade with the Cherokee. The expedition, which included Gabriel Arthur and James Needham, was a failure. It did not reach the Cherokee and on the journey back to Virginia they were attacked by Indians. Needham was killed and Arthur was seriously wounded. 

Gabriel Arthur was taken captive and adopted by a Cherokee tribe. For the next year, he lived with the Cherokee and traveled throughout the region. Arthur traveled as far north as the Ohio River and as far south as Spanish Florida. It is believed he is the first European to have visited the area of present-day West Virginia and crossed through the Cumberland Gap.

Dr. Thomas Walker Finds the Path Through the Cumberland Gap

The credit for discovering the route through Cumberland Gap belongs to Dr. Thomas Walker. He was a physician, planter, and explorer from Virginia. In 1749, he helped found the Loyal Land Company, which received a grant for 800,000 acres of land in Virginia, which is present-day southeastern Kentucky. The grant was awarded to the company by the House of Burgesses.

In 1750, Walker led a small expedition that initially found the path leading down Powell Valley, passing through the Cumberland Gap, and continuing through the gap at Pineville, where the Cumberland River cuts through Pine Mountain. At one point, they camped at present-day Paintsville, Kentucky, about 130 miles east of Lexington.

During the expedition, which included five other men, Walker named the Powell River, Cumberland Gap, and the Cumberland River a full 25 years before Boone blazed the Wilderness Road. 

The Cumberland River and the Cumberland Gap were named after the Duke of Cumberland. 

Walker and his men also built the first cabin in Kentucky during their expedition and met with Cherokee leaders. 

Christopher Gist and the Ohio Company

Gist explored the region, on behalf of the Ohio Company, which was a competitor of the Loyal Land Company. Gist was a frontiersman who lived on the Yadkin River in North Carolina.

The Ohio Company was formed in 1748 by John Hanbury, a London merchant, Thomas Lee, President of the Council of Virginia, and some other Virginia businessmen. On July 12, 1749, the company received a grant for 200,000 acres of land located between the Monongahela River and the Great Kanawha River.

Gist started his journey in October 1750. He traveled to the Ohio River and made his way west to present-day Bolivar, Ohio, which is in east central Ohio. From there, Gist went south into Kentucky and made his way into the mountains in the southeast of the region.

On the return journey, Gist followed Dr. Walker’s path and returned to North Carolina where he reported on the fertile lands he saw in Ohio and Kentucky. It is very likely the Ohio Company would have established settlements in the Ohio Valley if the French and Indian War had not started when it did.

Exploration Pauses During the French and Indian War

In 1753, the Loyal Land Company planned an expedition into the region for the purpose of finding a river known as “Missouri,” to see if it existed and connected to the Pacific Ocean. Overall, the goals of this planned expedition were similar to those of the Lewis and Clark Expedition that took place roughly 50 years later.

While the Loyal Land Company’s expedition would have likely used the path that became the Wilderness Road, the Lewis and Clark Expedition relied on water routes to travel from Kentucky to Missouri.

The Role of Braddock’s Campaign in the Wilderness Road

However, the outbreak of the French and Indian War in 1754 paused expeditions into Kentucky. Thomas Walker was involved in the war effort and helped support the expedition General Edward Braddock led into western Pennsylvania. Braddocks’ Expedition was destroyed at the Battle of the Monongahela (July 9, 1755).

Braddock’s defeat led to an increase in Indian raids against British settlements on the frontier, and settlers left their homes and returned to the safety of Virginia and other colonies on the coast. The demand for the land owned by the Loyal Land Company dropped and the company’s charter expired in 1757.

It is likely that Daniel Boone learned about the path that became the Wilderness Road to Kentucky from John Finley. Boone met Finley during Braddock’s Campaign, and Finley accompanied Boone on the expedition to Kentucky from 1769 and 1771. Finley is believed to have made his first trip into the region in 1752.

Pontiac’s Rebellion Affects the Wilderness Road

Following the end of the war, France ceded most of its territory in North America to Britain, as part of the 1763 Treaty of Paris. Indian tribes living in the Great Lakes Region and Ohio Valley Region decided to continue the fight. Led by Chief Pontiac, the tribes carried out Pontiac’s Rebellion, which consisted of a series of attacks against British forts and settlements.

Despite the conflict, Henry Scaggs passed through the Cumberland Gap in 1764 and hunted along the Cumberland River.

Pontiac, Illustration
This illustration depicts Chief Pontiac. Image Source: Wikipedia.

Americans Defy the Proclamation of 1763

In an effort to appease the Indian Tribes and bring an end to the conflict, King George III issued the Royal Proclamation of 1763, which prohibited settlers from living west of the Appalachian Mountains. It also reserved most of the land between the Appalachians and the Mississippi River as hunting grounds for the Indians.

Despite the Proclamation, James Smith and his party of five entered Kentucky in 1766 through the Cumberland Gap, while another group of five hunters led by Isaac Lindsey journeyed to Kentucky from South Carolina.

A year later, in 1767, explorers James Harrod and Michael Stoner reached the southeastern part of Kentucky. John Finley also hunted and traded in the area the same year.

King George III, Painting
King George III. Image Source: Wikipedia.

The 1768 Treaty of Fort Stanwix Opens the Wilderness Road

The turning point in the exploration of Kentucky came in 1768 with the Treaty of Fort Stanwix. According to the treaty, the Iroquois Confederacy relinquished their claims to the land between the Ohio and Tennessee Rivers, effectively granting Virginia rights to the Kentucky territory.

The Wilderness Road Leads the Long Hunters into Kentucky

Soon after, the exploration of Kentucky increased, notably with hunting expeditions carried out between 1769 and 1771. During these years, men known as “Long Hunters” ventured into Kentucky through the Cumberland Gap. 

There, deep in the forest of the region, they hunted for many months along the Cumberland River and Green River in the southern part of present-day Eastern Kentucky.

As a result, the route for the Wilderness Road had become well-known among men familiar with the region.

Joseph Martin Establishes Martin’s Station

Joseph Martin, who worked for Thomas Walker, made his first trip into the region in 1769. Martin led and traveled to Powell’s Valley where he and the men with him built Martin’s Station at present-day Rose Hill, Virginia. Martin and his men were forced to abandon the fort after an Indian attack and return to Virginia. However, Martin would return in 1775, acting as an agent for Richard Henderson.

Daniel Boone’s Early Trips on the Wilderness Road

Daniel Boone likely spent more time in Kentucky than any other American, prior to its settlement. His aspirations for Kentucky date back to 1767 when he attempted to access the region by crossing the valleys of the Holston River and Clinch River, aiming to reach the headwaters of the west fork of the Big Sandy River and then following it to the Ohio River. Unfortunately, he failed to reach his intended destination and returned home.

In 1769, Boone led another expedition into Kentucky and hunted along the Kentucky River, making his way into Central Kentucky.

Boone was accompanied by five others, including John Finley. Their journey started on May 1, 1769. Later, Squire Boone, Daniel’s brother, joined the expedition, alternating with Daniel in Kentucky until the spring of 1771.

Boone’s hunting expedition, which lasted from 1769 to 1771, is considered by many to be the most significant moment in the exploration of the state. The expedition led to the discovery of the fertile lands of Central Kentucky and the route through the mountains — the Cumberland Gap.

Between 1771 and 1773, it is likely that Boone made two additional trips to Kentucky. 

In June 1774, Boone and Michael Stoner undertook a trip to the Falls of the Ohio River, serving as agents for Governor Dunmore. Their mission was to warn settlers in Kentucky of the outbreak of Indian hostilities. On this journey, Boone and Stoner covered the distance on foot, traveling from the Clinch River to the Falls of the Ohio and back in just 62 days.

Daniel Boone, Portrait, Harding
Daniel Boone in his later years. Image Source: National Portrait Gallery.

The Settlement of Kentucky Begins with Harrodsburg

In 1774, James Harrod and a group of 35 settlers attempted to establish a settlement at Harrodsburg. However, they abandoned it when they received news from Boone and Stoner regarding the threat of an Indian attack.

Daniel Boone Blazes the Wilderness Road

No one is more closely associated with Kentucky and the Wilderness Road than Daniel Boone. However, it was another man, Colonel Richard Henderson, who paved the way for Boone to blaze the Wilderness Road.

Richard Henderson and the Transylvania Colony

Colonel Richard Henderson envisioned the creation of his own proprietary colony in Kentucky, similar to Maryland and Pennsylvania. Henderson called his venture Transylvania Colony, but it failed to last. His company was dissolved in December 1776, roughly a year and a half after the establishment of Boonesborough. However, Henderson played an important role by providing organized support to the early settlements of 1775.

Fort Boonesborough, Kentucky, Illustration
This illustration depicts the fort at Boonesborough. Image Source: Daniel Boone by Reuben Gold Thwaits,

The Treaty of Sycamore Shoals

In February 1775, Henderson and others, including Boone, met with the Cherokee leaders at Sycamore Shoals, located at Watauga. 

On March 17th, they agreed to the Treaty of Sycamore Shoals, and Henderson bought the land between the Kentucky River and Cumberland River for 10,000 pounds sterling. Henderson was also given permission for settlers to travel through their Cherokee territory from Virginia to the new settlements.

Soon after, Henderson set in motion his plan to settle his colony. Having already agreed to work for Henderson, Boone was responsible for leading an expedition to Kentucky, locating a trail, scouting for a site for the Transylvania settlement, and overseeing its establishment.

Pioneers Move Into Kentucky

In the spring of 1775, Harrod and the settlers returned to Harrodsburg. 

Meanwhile, Boone took charge of leading the Transylvania expedition to establish a new settlement, which would be called  Boonesborough. 

Harrod was about a month ahead of Boone of Boone’s expedition and arrived in Kentucky first.

Between Harrodsburg and Boonesborough, it is estimated there were somewhere between 100-300 American settlers living in all of Kentucky.

The Wilderness Road through the Cumberland Gap

In a letter addressed to Governor Isaac Shelby, Boone asserted, “I first marked out that road in March 1775.”

Boone led a party of 30 to 35 men on the expedition into Kentucky. Some of the men who joined him were his brother, Squire Boone, along with Michael Stoner, Richard Callaway, William Bush, David Gass, and Felix Walker. Before the expedition set out, the men agreed to follow Boone as the leader. Walker kept a journal of the expedition, and wrote the men were “under the management and control of Colonel Boone, who was to be our pilot and conductor through the wilderness to the promised land.”

They left on March 10th, commencing their journey from Long Island, which was just above the mouth of the South Fork of the Holston River. Boone followed the Clinch River and Powell River and made his way to Martin’s Station, about 20 miles east of the Cumberland Gap.

Beyond the point where the trail was already defined, Boone proceeded to mark the path by blazing trees. Blazing the trail involved making distinctive markings on trees to indicate the route, ensuring that future travelers could follow the path.

Boone’s initial road was called “Boone Trace” or “Boone’s Road.”

Wilderness Road, Daniel Boone Blazing the Trail, Illustration, NA
This 1938 illustration by Carl Rakeman depicts Boone and his men blazing the Wilderness Road. Image Source: National Archives.

Boone and his men cut the Wilderness Road with their axes, so it was really nothing more than a rough, marked path that ran from Long Island to Boonesborough. On March 24, Boone’s expedition reached the location of Fort Estill, just 15 miles from the site where Boonesborough would be established. In two weeks, Boone and his men traveled 200 miles through the wilderness and marked the Wilderness Road.

Boone Trace was initially just a walking path, but as more and more settlers began to use the route to move west, it was widened and improved in the 1790s.

Indian Attack at Fort Estill

The journey became more difficult when they entered the Kentucky mountains. They turned north and moved northwest, off the trail, near Rock Castle River. According to one of the men, Felix Walker, they had to carve their way through canebrakes and thick underbrush for 20 to 30 miles, cutting their way through previously uncharted wilderness.

Early on the morning of March 25, at the location of Fort Estill, near present-day Richmond, Kentucky, the expedition was attacked by a party of Shawnees. The men were still sleeping when the attack came. Two men were killed, and Felix Walker was seriously wounded.

Boone reported the incident, saying, “We stood on the ground and guarded our baggage till day and lost nothing. We have about fifteen miles to Kentuck.”

They still had approximately 15 miles to cover until they reached their destination, the Kentucky River at Otter Creek. The Indian attack forced Boone to pause the expedition for nine days. 

Eventually, on April 6th, 1775, they resumed their journey, arriving at the mouth of Otter Creek on the Kentucky River.

Henderson Follows Boone on the Wilderness Road

Colonel Henderson set out from Watauga on March 20th. It is believed he had roughly 30 others with him. The expedition successfully made its way to Martin’s Station and was eventually joined by more settlers. Henderson’s expedition reached Boonesborough on April 20th. 

Benjamin Logan Cuts a Path to the Falls of the Ohio

As Henderson’s expedition approached Rock Castle River, he turned northward towards Boonesborough. At that point, another group within the party, led by Benjamin Logan and including some members who had joined Henderson in Powell Valley, continued their northwestward journey along an older trail, known as Skaggs Trace.

General Benjamin Logan, Portrait
General Benjamin Logan. Image Source: Google Arts & Culture.

Logan’s party traveled to the present-day site of Stanford, where they established Logan’s Fort, also known as St. Asaph. The trail leading to Logan’s Fort, which was on the route to the Falls of the Ohio, subsequently evolved into a prominent road leading to Central Kentucky. 

This road passed through key settlements such as Crab Orchard, Stanford, Danville, Harrodsburg, Bardstown, and the Salt Works near Shepherdsville, eventually leading to Louisville. 

The trail to Crab Orchard, marked out by the pioneering efforts of Boone and Logan, persisted as the Wilderness Road to Kentucky during the era of westward expansion.

Kentucky on the Frontier

Kentucky emerged as an important state in terms of America’s Manifest Destiny. In the vast wilderness that stretched from the Great Lakes to the Gulf of Mexico and from the Allegheny Mountains to the Mississippi River, Kentucky was the only place on the frontier where American settlements thrived.

Still, they were at least 200 miles away from the western outposts of the eastern Colonies and separated by 500 miles from the older eastern settlements. 

Within this 200-mile stretch of wilderness, Kentucky had two routes of communication with the eastern Colonies. The first was via mountain roads leading to Pittsburgh and then downstream along the Ohio River. The second was through Cumberland Gap via the Wilderness Road.

Fort Boonesborough, 2023, AHC
This photograph shows the present-day location of Fort Boonesborough. Image Source: American History Central.

Growth of Kentucky and Statehood

By 1783, it is estimated there were 12,000 Americans in Kentucky. By that time, the American Revolution was over, and the presence of those 12,000 settlers played an important role in securing Kentucky, Ohio, Indiana, and Illinois for the United States.

Within a year, the population of Kentucky reached 20,000. During 1784, 30,000 immigrants, including men, women, and children, are believed to have traveled into Kentucky via the Wilderness Road from Virginia and North Carolina.

By the time of the 1790 census, Kentucky’s population exceeded 75,000. Over the next decade, the population significantly increased to approximately 990,000. It was one of the fastest-growing states in the Union.

In 1790, it ranked 14th among the 16 states and territories in terms of population. However, by 1800, it had 9th place, surpassing four of the 13 Original Colonies. 

Further, the 1790 census reported a total population of 4,280 for the entire territory north of the Ohio River. Marietta and Cincinnati, which were the oldest colonial settlements in the Western region north of the Ohio River, were founded in 1788. 

On June 1st, 1792, Kentucky had achieved statehood.

Marietta, Ohio,1791, Illustration
This illustration depicts Marietta around 1791. Image Source: Wikipedia.

Popularity of the Wilderness Road

The Wilderness Road, as it became known, was a crucial route for westward expansion and the settlement of Kentucky. It was mentioned in John Filson’s famous 1784 map of “Kentucke” as “The Road from the Old settle[ments] thro’ the great Wilderness.” and the first true mention of the Wilderness Road was in Lexington, “Kentucky Gazette” on October 15, 1796, which stated that “The Wilderness Road from Cumberland Gap to the settlements in Kentucky is now compleated. Waggons loaded with a ton of weight, may pass with ease, with four good horses.”

The Wilderness Road through the Cumberland Gap was the preferred way for travelers from the lower Ohio Valley to travel east. 

The land route to western destinations like St. Louis and Vincennes also passed through the Cumberland Gap 

Improvements to the road, such as widening it to accommodate wagons, were made as Kentucky became a state in 1792.

As the Wilderness Road became more accessible to wagons, enterprising merchants loaded them up with goods and headed west to facilitate commerce. Settlers from Kentucky, in turn, drove cattle and horses back east for sale. 

The Battle of Fallen Timbers Opens Ohio

Despite the existence of the Ohio settlements, most of the area north of the Ohio River was considered too risky for settlement. It was associated with the threat of Indian attacks and a difficult westward journey. 

The settlement of the territory north of the Ohio River did not really begin until 1795, following the Battle of Fallen Timbers in 1794. 

General Anthony Wayne’s victory over the Indians in that battle effectively opened up the region for American settlement and the Ohio River became a significant route for settlers to use to travel into the region.

General Anthony Wayne, Portrait
General Anthony Wayne. Image Source: New York Public Library Digital Collections.

The Importance of the Wilderness Road to Kentucky

Following the settlement of Kentucky, the Wilderness Road served as the main route connecting Kentucky to the east for 20 years. The region was settled via the Wilderness Road, and it is estimated that at least 300,000-400,000 pioneers used it to make their way to Kentucky.

Those people carried with them the culture, knowledge, and customs that formed the American identity, and when they reached Kentucky, they laid the foundation for a state that quickly grew to rival those on the East Coast.

The Wilderness Road helped shape Kentucky, opening the path to the western frontier.

Wilderness Road, Map, NPS
This map shows the route of the Wilderness Road. Image Source: National Park Service.

Facts About the Dangers of the Wilderness Road

  • The Wilderness Road was an extremely dangerous path for settlers to travel. Not only did settlers have to be prepared to defend themselves from Indian attacks, but also from attacks by thieves.
  • Over time, blockhouses were built along the road, so settlers could take refuge in the case of danger.
  • Chickamauga Indians, led by Dragging Canoe, were known to ambush groups of immigrants along the Wilderness Road.
  • Settlers were also vulnerable to attacks from animals, including wolves and panthers. There were also dangerous snakes like copperheads and rattlesnakes along the route of the Wilderness Road.
Fort Boonesborough, Sycamore Hollow Marker, 2023, AHC
The Sycamore Hollow historic marker at the location of Fort Boonesborough. Image Source: American History Central.

The Wilderness Road and Kentucky During the American Revolutionary War

During the American Revolutionary War, the settlement of Kentucky attracted the attention of the British, who recognized the threat the settlements posed on their southern flank. 

British Outposts on the Frontier at the Start of the American Revolutionary War

Following the French and Indian War, Great Britain controlled important outposts in the region, spanning territory from the Tennessee River to the Great Lakes and from the Mississippi River to the west.

To the north of the Ohio River, this territory was inhabited by Native American Indians. It was the same south of the Tennessee River. Between the Ohio River and the Tennessee River, the land was largely uninhabited, but it was used as hunting grounds by various Indian tribes.

In the Northwest Territory, British outposts extended westward along the Great Lakes, reaching as far as Mackinac. Detroit served as their primary base of operations. 

Moving southwest, the British presence extended as far as Kaskaskia and Cahokia along the Mississippi River, with Vincennes on the Wabash River also serving as a prominent outpost. 

This distribution of British outposts gave them a strategic advantage because they encircled the American Colonies and also allowed British officials to manage their alliances with the Indians. Ultimately, the location of British outposts and alliances with the Indians would cause significant difficulties for settlers living on the frontier of the colonies.

Colonial Outposts on the Frontier at the Start of the American Revolutionary War

The Colonial outposts did not extend as far west as those of the British. The westernmost outpost was the fort at present-day Pittsburgh. Known as Fort Duquesne and then Fort Pitt, it was abandoned in 1772, but rebuilt in 1774 and renamed Fort Dunmore.

On the road to Fort Dunmore was Fort Cumberland, at present-day Cumberland, Mayland. It was a stopping point on the route to Pittsburgh. While there were small, struggling settlements in the Shenandoah Valley, aside from Pittsburgh, the only settlements located west of the Allegheny Mountains were those situated on the headwaters of New River and in the Holston Valley in western Virginia and Clinch Valley in western North Carolina.

Settlers from Virginia and North Carolina had made the most significant westward progress, establishing a settlement on the headwaters of the Holston River, which later became the Watauga Settlement.

The pioneers living in the western settlements of Virginia and North Carolina lived much further from the coast than those in New England and some of the Middle Colonies. The westernmost settlements in colonies like New York, Pennsylvania, and Maryland were still 100 miles or less from the Atlantic Coast.  Watauga is located near present-day Elizabethton, Kentucky, which was roughly a 400-mile journey to Wilmington, North Carolina in the 1770s.

British Attacks on Settlements in Kentucky

From 1775 to 1782, the British made persistent efforts, often through their Indian allies, to eliminate the settlements. However, the settlements were able to survive through the efforts of their militia forces. 

The militia forces, which are referred to as the Overmountain Men, won one of the most important victories for American forces during the war when they defeated British forces at the Battle of Kings Mountain (October 7, 1780).

Battle of Kings Mountain, Death of Patrick Ferguson
This illustration depicts the death of Major Patrick Ferguson at the Battle of Kings Mountain. Image Source: New York Public Library Digital Collections.

Later Years of the Wilderness Road

As demand for improvements increased with the growing number of settlers and commercial traffic, the Wilderness Road became the most direct and easiest path from the lower Ohio Valley to Philadelphia until the opening of the Erie Canal and roads across the mid-Atlantic states in the 1830s. Overall, the emergence of canals and railroads reduced the usage of the Wilderness Road.

At the height of its popularity, the road served as a major route for livestock herders, who drove their herds from Kentucky to the southeastern states.

Starting in 1792, the Wilderness Road was used as a postal road, which improved communication with the East Coast. The postal route ran from Bean Station, Tennessee through the Cumberland Gap, along the Wilderness Road, to Danville, Kentucky.

The advent of the National Road in the 1830s and the construction of the Erie Canal made the Wilderness Road less of a first choice for settlers heading west. By 1850, the road was largely abandoned.

The Wilderness Road and Cumberland Gap During the Civil War

During the Civil War, the Wilderness Road was used by forces from the United States and Confederate States. 

Confederate forces tried to take control of Kentucky early in the war but were defeated at the Battle of Camp Wildcat.

The region alternated between control of Union and Confederate forces at least four times during the war.

Legacy of the Wilderness Road

Portions of the Wilderness Road were some of the first roads to be paved in the United States. The first portion ran from Cumberland Gap, Tennessee to Middlesboro, Kentucky, and was finished in 1908.

Cumberland Gap is a National Historical Park, managed by the National Park Service. It is located along the borders of Kentucky, Tennessee, and Virginia.

Wilderness Road Significance

The Wilderness Road is important to United States history for the crucial role it played in the settlement of Kentucky and the expansion of the United States, providing a pathway for pioneers and settlers to the western frontier.

Wilderness Road Timeline

This timeline of the Wilderness Road connects the discovery and establishment of the road to significant moments in American History that are related to the founding of the United States and America’s Westward Expansion.

1600s — The path through the Cumberland Gap starts as an animal path, and is used by Indian tribes including the Delaware in Pennsylvania, and the Shawnee and Yuchi in Virginia.

1607 — English settlers establish Jamestown, Virginia, the first permanent English settlement in America.

1654 — Abraham Wood travels into the Southwest region of Virginia from Fort Henry. He makes his way 120 miles to the town of the Occaneechi, which sits at the junction of the Roanoke River and Dan River.

1669–70 — Dr. John Lederer, a German physician, journeys to the top of the Blue Ridge Mountains at Front Royal.

1671 — Abraham Wood funds an expedition led by Captain Thomas Batts and assistant Robert Fallam. For the first time, explorers reach the Appalachian divide and find the Indian trail known as the Great Warrior’s Path. The expedition encounters the Totero tribe during the journey.

1673 — Abraham Wood sends James Needham and his assistant Gabriel Arthur to the Cherokee capital at Chota in present-day Tennessee. Arthur is held captive by Indians and travels with them for more than a year. He is believed to have been the first European to pass through the Cumberland Gap.

1675Bacon’s Rebellion begins in the Province of Virginia.

1676Nathaniel Bacon and his army burn most of the buildings in Jamestown, Virginia.

Bacon's Rebellion, Burning Jamestown
This illustration depicts the Burning of Jamestown that took place during Bacon’s Rebellion. Image Source: New York Public Library Digital Collections.

1681–1698 — Colonel Cadwallader Jones establishes trade with Indians beyond the Blue Ridge Mountains.

1706 — Franz Ludwig Michel of Bern, Switzerland explores the Shenandoah Valley.

1716 — Governor Alexander Spotswood leads his “Knights of the Golden Horseshoe” over the Blue Ridge Mountains and into the Shenandoah Valley.

1738 – Augustana County is established in Virginia. At the time, the settlements in the county are the furthest west in Colonial America.

1739 – Benjamin Borden receives a grant of 92,000 to bring settlers into the area of present-day Rockbridge County, Virginia.

1742–1745 – Colonel James Patton receives two land grants of 100,000 acres each to settle the Roanoke River Valley and New River Valley.

1744 — The Treaty of Lancaster with the Iroquois Confederacy allows English settlements west of the Allegheny Mountains and use of the Great Warriors’ Path.

1745 — The first settlement west of the New River is established. It is called “Dunkards Bottom” because it is founded by German immigrants known as Dunkards.

1749 — Dr. Thomas Walker partners with a group of men, including Peter Jefferson, the father of Thomas Jefferson, to form the Loyal Land Company.  A year later, Walker leads his expedition through the Cumberland Gap.

1751 — Joshua Fry and Peter Jefferson publish a map listing several names for the route, including “Indian Road by Treaty of Lancaster” and the “Great Road thro Virginia to Philadelphia.”

1754 — The French and Indian War begins and many settlers flee eastward to safety.

1755 — Shawnee warriors attack the settlement at Draper’s Meadow in present-day Blacksburg, Virginia. Colonel James Patton is killed and Mary Draper Ingles is taken captive. 

1755–1756 — Fort Vause is built near Shawsville along the Wilderness Road in response to Indian attacks and the return of Mary Draper Ingles. Later, the fort is captured and burned by the French and their Indian allies.

1756 — Colonel George Washington oversees the reconstruction of Fort Vause. At one point, Washington is almost captured and killed by Shawnee warriors traveling north on the Wilderness Trail.

1758 — The Wilderness Road is called the Valley Road in the Shenandoah Region. Some call it the “Pennsylvania Road” or the “Irish Road.”

1758 — Fort Chiswell is built by Colonel William Byrd III near present-day Wytheville, Virginia. It will be used as a staging point for the military during the “Cherokee Wars.”

1758 — Three companies under the command of Major Andrew Lewis widen the portion of the Wilderness Road from the crossing on the New River to present-day Abingdon, so it is wide enough for wagons.

1761 — Elisha Walden and an expedition of Long Hunters leave Fort Chiswell. They intend to explore and hunt in the area west of the Cumberland Gap. Although they are unable to go as far as planned, their successful hunt inspires more Long Hunters to travel to Kentucky.

1761 — William Ingles acquires a license to operate a ferry “over the New River to the opposite shore.” Ingles Ferry is located near the present-day city of Radford, Virginia.

1763 — The French and Indian War is ended by the Treaty of Paris. Soon after, the British government decides to keep a standing army in North America, which is used to garrison the frontier outposts and defend the newly acquired territory. In 1764, Parliament passes the Sugar Act, which is intended to help raise money to pay for the standing army. Passage of the Sugar Act incites unrest, marking the beginning of the American Revolution.

1769 — Joseph Martin is recruited to explore the Powell Valley, just a few miles from Cumberland Gap.

1769 — Daniel Boone and a group of Long Hunters encounter Joseph Martin in Powell Valley. Boone follows the hunting path into Kentucky and establishes a camp. Boone hunts the region for nearly two years.

September 1773 — Daniel Boone and William Russell try to move their families to Kentucky. During the journey, Boone’s son James and Russell’s son Henry, along with some others, are killed in an Indian attack. Boone and Russell abandon the journey. The attack is one of the causes of Lord Dunmore’s War.

1773–1774 — Daniel Boone and his family spend the winter at Castle Wood on the Clinch River.

1774 — Lord Dunmore orders the construction of forts along the Clinch River.

April 30, 1774 — The Yellow Creek Massacre takes place. Settlers kill a group of Mingo Indians who are related to the chief of the Mingo, Logan. Before the incident, Logan was on good terms with the English. The incident led to the outbreak of Lord Dunmore’s War.

October 10, 1774 — Colonel Andrew Lewis leads provincial forces to victory at the Battle of Point Pleasant in present-day West Virginia. The victory ends the war with the Shawnee and opens Kentucky to settlement.

1775 — Colonel Richard Henderson of the Transylvania Land Company signs a treaty to purchase land from the Cherokee. He hires Daniel Boone to blaze a trail through the Cumberland Gap into Kentucky.

March 10, 1775 — Daniel Boone begins the journey to Kentucky, blazing the Wilderness Road.

April 19, 1775 — The American Revolutionary War begins with the Battle of Lexington. By the end of the day, Massachusetts Militia forces fought the British at the Battle of Concord, Parker’s Revenge, and the Battle of Menotomy. The day ends with British forces under siege in Boston, trapped by thousands of militia from Massachusetts and other New England Colonies

1776 — The American Colonies declare their independence from Great Britain.

1780 — The Overmountain Men meet at Sycamore Shoals on the Watauga, then march to Kings Mountain, where they defeat British forces led by Patrick Ferguson. The Patriot victory at Kings Mountain is a turning point of the war, and contributes to British forces under the command of General Charles Cornwallis abandoning plans to invade North Carolina.

1783 — Great Britain recognizes the independent United States of America.

1784 — Teacher and explorer John Filson writes about the Wilderness Road and the exploits of Daniel Boone in his book The Discovery, Settlement, and Present State of Kentucke. The book inspires many Americans to move west.

April 23, 1784 — Congress passes the Ordinance of 1784, which defines the process for a territory to become a state.

1785 — Congress passes the Land Ordinance of 1785, which organizes the Northwest Territory.

1787 — Congress passes the Northwest Ordinance of 1787, which defines a Bill of Rights for the Northwest Territory, along with a process for a territory in the region to become a state.

1787 — The Constitutional Convention in Philadelphia creates the United States Constitution.

1788 — The United States Constitution is ratified. Later in the year, George Washington is elected first President of the United States.

June 12, 1792 — Kentucky becomes the 15th state in the Union.

Fort Boonesborough, Divine Elm Marker, 2023, AHC
The Divine Elm historic marker at the location of Fort Boonesborough. Image Source: American History Central.

August 20, 1794General Anthony Wayne leads American forces to victory over the Northwest Indian Confederacy at the Battle of Fallen Timbers. The victory opens the Northwest Territory to settlement north of the Ohio River.

1795–1796 — The Kentucky portion of the Wilderness Road is improved and opened to wagon travel.

1803The United States and France agree to the Louisiana Purchase.

1804–1806 – The Lewis and Clark Expedition explores and maps the upper portion of the Great Plains, from St. Louis to the Pacific Ocean.

1805–1806Zebulon Pike leads an expedition to find the source of the Mississippi River. A second expedition explored the American southwest.

Wilderness Road APUSH, Review, Notes, Study Guide

Use the following links and videos to study the Wilderness Road, Daniel Boone, and Manifest Destiny for the AP US History Exam. Also, be sure to look at our Guide to the AP US History Exam.

Wilderness Road APUSH Definition

The Wilderness Road was an early road through the Cumberland Gap and into Kentucky that was formed and used by settlers traveling westward in the late 1700s. It was blazed by Daniel Boone and improved over the years as more settlers traveled into Kentucky. Despite the rough terrain and shortage of supplies, thousands of families journeyed on the Wilderness Road seeking farmland and new opportunities in the West during the major westward migration of early American settlers.

Wilderness Road Video for APUSH Notes

This video from the Smithsonian Channel discusses Daniel Boone and the Wilderness Road.

Citation Information

The following information is provided for citations, including APA Style, Chicago Style, and MLA Style.

  • Article Title The Wilderness Road — Daniel Boone’s Path into Kentucky
  • Date 1607–1865
  • Author
  • Keywords Wilderness Road, Daniel Boone, Cumberland Gap
  • Website Name American History Central
  • Access Date May 22, 2024
  • Publisher R.Squared Communications, LLC
  • Original Published Date
  • Date of Last Update March 26, 2024