Throughout the ages, poets, songwriters, novelists, journal writers, historians and artists have captured the grandeur of the Cumberland Gap. James Smith, in his journal of 1792, penned what is perhaps one of the most poignant descriptions of this national and historically significant landmark: "We started just as the sun began to gild the tops of the high mountains. We ascended Cumberland Mountain, from the top of which the bright luminary of day appeared to our view in all his rising glory; the mists dispersed and the floating clouds hasted away at his appearing. This is the famous Cumberland Gap..." Thanks to the vision of Congress, who in 1940 authorized Cumberland Gap National Historical Park, visitors today can still bask in its beauty and immerse themselves in its rich history.

The story of the first doorway to the west is commemorated at the national park, located where the borders of Tennessee, Kentucky, and Virginia meet. Carved by wind and water, Cumberland Gap forms a major break in the formidable Appalachian Mountain chain. First used by large game animals in their migratory journeys, followed by Native Americans, the Cumberland Gap was the first and best avenue for the settlement of the interior of this nation. From 1775 to 1810, the Gap's heyday, between 200,000 and 300,000 men, women, and children from all walks of life, crossed the Gap into "Kentuckee."

It was not until 1750 that Dr. Thomas Walker, surveyor for the Loyal Land Company, became the first to explore, describe, and document the route to the Gap; which he named in honor of William, Duke of Cumberland, brother of King George II. In 1775, a little known longhunter named Daniel Boone was commissioned to blaze a road through the Gap. Boone's Trace evolved into the Wilderness Road, establishing his place in history as a frontiersman and pathfinder. During the dark and dangerous days of the Revolution, the settlements in Kentucky, headed by men like Boone and James Harrod, maintained a toehold in the wilderness, securing claim to the western lands for the young nation.

The importance of the Gap in the post-Revolutionary period is of major significance. The discovery and use of Cumberland Gap released a floodtide of settlers into the lands of the interior. A mere ten years after the end of the Revolution, Kentucky became the 15th state boasting a population of 220,000. Though other routes were utilized, Cumberland Gap was "the way West" until 1810. In the 20th Century, Cumberland Gap (and its associated roadways) continued to be a major economic artery for the Appalachian region. Modernization of the roadways began in 1908 with the completion of the "Object Lesson Road"; a Federal demonstration project by the Bureau of Public Roads. This road opened the Gap to commercial traffic. In the 1920s the old Wilderness Road became Highways 25E and 58, allowing mechanized traffic through the Gap.