Middlesboro, KY
Discovery Trail KY Heritage Tour Heritage Trail
1000-Mile Front
CUMBERLAND GAP NATIONAL HISTORIC PARK: The historic Wilderness Road that opened Kentucky for early settlement passes through Cumberland Gap.   During the Civil War, control of this important entrance into Kentucky was hotly contested.  Both sides constructed numerous fortifications in the area, and the Gap changed hands four times.  Many of the earthworks, such as Fort McCook, can still be seen today.  With 20,305 wilderness acres, this is the largest National Historical Park in the country.  Begin your adventure at the visitor center, which has an orientation program and museum. Pinnacle Overlook features a panoramic view of three states. 

Near the Pinnacle overlook is Fort Lyon, the site of the final surrender of the Gap to the Union on September 9, 1863.  This surrender left an indelible impression on Confederate commander Lt. William R. McEntire.  His dying wish in 1917 was to have his grandson promise to return to the Gap on the 100-year anniversary of the surrender, stand at the Pinnacle, and curse the Yankees for five minutes.   The grandson kept his promise.


  • A Masterful Retreat (State Marker 521, Cumberland Gap, US 25E)
  • Colonel Arthur Campbell (State Marker 129, US 25E, Middlesboro)
  • Invasion and Retreat (State Marker 683, US 25E, Pineville)

    For additional information:

    WMTH Corporation, PO Box 51153, Bowling Green, KY 42102