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  1. The notch can be seen from the Powell Mountain Overlook west of Duffield on Rte 58, or visitors can climb to the gap along the Daniel Boone Trail, a section of the Virginia Birding and Wildlife Trail.

    • The Great Road

      The Great Road. The Valley of Virginia has been occupied for...

    • Frontier Trail

      Frontier Trail. In the mid-eighteenth century, access to...

    • Fincastle Turnpike

      The Cumberland Gap Road (known as the Fincastle Turnpike),...

    • Crossroads

      The historic road divides into the sections known as the...

    • Carolina Road

      Carolina Road. Highway 220 follows in the steps of the...

    • History Behind The Wilderness Road
    • Daniel Boone & The Transylvania Company
    • Blazing A Historic Trail
    • Westward Movement

    The earliest origins of the Wilderness Road were the traces, or trails, created by the great herds of buffalo that once roamed the region. Native American tribes such as the Cherokee and Shawnee later used the trails to make attacks on each other. They called the path the Athowominee, variously translated as “Path of the Armed Ones” or “The Great W...

    Born in Pennsylvania in 1734, Daniel Boone moved with his family to the North Carolina frontier as a youth. He fought in the French and Indian War, and later served two terms in the Virginia General Assembly. Boone first ventured through the Cumberland Gap on a hunting expedition in 1767. In 1773, he sought to lead his family and several others to ...

    On March 10, 1775, Boone and around 30 other ax-wielding road cutters (including his brother and son-in-law) set off from the Long Island of Holston River, a sacred Cherokee treaty site located in present-day Kingsport, Tennessee. From there they traveled north along a portion of the Great Warrior’s Path, heading through Moccasin Gap in the Clinch ...

    The opening of the Wilderness Road enabled the founding of the first settlements in Kentucky, including Transylvania Colony–which became Boonesboro–Harrod’s Town and Benjamin Logan’s. After the outbreak of the Revolutionary Warthat same year, the rush towards western settlement began, and it would continue throughout the war and beyond. As many as ...

  2. Wilderness Road Trail spans 8.5 from Old Wilderness Road/US 58 (TN-VA state line) to Daniel Boone Trail Rd./US 58 (near Ewing). View amenities, descriptions, reviews, photos, itineraries, and directions on TrailLink.

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    • Wilderness Road Trail, Lexington-Fayette, KY, Virginia
  3. Aug 8, 2024 · Wilderness Road State Park gives guests a chance to enjoy mountain biking, a self-guided hiking trail, picnic shelters, and interpretive and environmental education programs.

  4. The Wilderness Road was one of two principal routes used by colonial and early national era settlers to reach Kentucky from the East.

  5. The Wilderness Road Trail at Cumberland Gap National Historical Park near Cumberland Gap, Virginia is an easy 1.4 mile out-and-back hike that leads from the Daniel Boone visitor center west toward the Gap Cave Trail and the Tennessee Road Trail to the Iron Furnace.

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  7. Several historical stops are available along the route, and it makes a great day-long road trip through the scenic rolling hills and valleys of Scott County, VA into Lee County, VA to the Cumberland Gap into Kentucky. Travelers may begin their journey at any juncture along the Wilderness Road.

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