Skip to main content
Friday, October 30, 2026Oct 30

This story is free to read.

Chattanooga-based travelers explore the Cumberland Gap, where Tennessee, Kentucky and Virginia converge

Contributed Photo by Patti Smith / The town of Cumberland Gap, Tenn., as seen from "The Pinnacle," a rock outcropping high above. Note the Airstream trailers arrayed along the main street.
Contributed Photo by Patti Smith / The town of Cumberland Gap, Tenn., as seen from "The Pinnacle," a rock outcropping high above. Note the Airstream trailers arrayed along the main street. Contributed Photo by Patti Smith / The town of Cumberland Gap, Tenn., as seen from "The Pinnacle," a rock outcropping high above. Note the Airstream trailers arrayed along the main street.

Our Eastern Tennessee Airstream Club recently rallied in the little town of Cumberland Gap, Tennessee – where Tennessee, Kentucky and Virginia converge. A volunteer community booster group called Guardians of the Gap coordinated “Streamin’ the Gap,” and it was spectacular. Mary Mars, Tony Maxwell and all the Guardians could not have been better hosts.

They arranged electrical hookups and parking for 20 Airstream trailers right in the middle of town, a hundred yards from the venerable Wilderness Road. Restaurants, shopping, parks and beautiful mountains surrounded us. Our hosts served a great dinner in a nearby park and arranged speakers, movies, games, live music and several tours during our three-day stay.

Their hospitality was only exceeded by the beauty and history of the area itself. The formidable ridge extending from Kentucky into Alabama and the narrow gap through it was named in 1750 by Dr. Thomas Walker. The gap, traversed for centuries by migrating buffalo and then by Indian hunting and war parties, was called Ouasiota by the local Indians; however, Walker named it after the British Army commander-in-chief, the Duke of Cumberland.

A member of Walker’s exploration group, John Findlay, relayed details of the area to a Quaker blacksmith and teamster (wagon driver) named Daniel Boone. The strapping young man ventured into the mountains of western Virginia and North Carolina and soon discovered the critical gap offering access to the beautiful lands of Kentucky. He brought back tales of fertile river valleys, bountiful game and accessible timber available to anyone willing to work hard and brave the wilderness. Boone joined with several wealthy men, who sponsored his endeavor, to attract new settlers. Soon, he and his men hacked a rough road through the gap from Virginia into Kentucky. Although it could not accommodate wagons, people and pack animals could negotiate the route variously called Boone’s Trace, the Transylvania Trail and, eventually, the Wilderness Road.

The road was more than a path from civilization to wilderness. Since Roman times, those who built roads into an isolated area claimed access, if not ownership, of that area. Hence, Daniel Boone’s Road, which initially attracted a few hardy souls, eventually opened the region we now know as Kentucky and Tennessee. Although there were treaties and laws meant to limit expansion, the flow of land-hungry settlers continued. The Indian chiefs had no legal authority to sell their people’s land, and the settlers, most of whom were British subjects, didn’t have the legal right to buy it. It made little difference. After the Revolutionary War, the trickle of immigrants turned into a flood. Historians estimate at least 250,000 European immigrants and perhaps as many as 300,000 made their way west through the Cumberland Gap.