U.S. Route 58 is an east–west U.S. Highway that runs for 508 miles (818 km) from U.S. Route 25E just northwest of Harrogate, Tennessee, to U.S. Route 60 in Virginia Beach, Virginia. Until 1996, when the Cumberland Gap Tunnel opened, US 58 ran only inside the commonwealth of Virginia. It was then extended southwest along a short piece of former US 25E, which no longer enters Virginia, to end at the new alignment in Tennessee. For most of its alignment, it closely parallels Virginia's southern border with North Carolina.

The Cumberland Gap Tunnel is a dual-bore, four lane vehicular tunnel that carries U.S. Route 25E under Cumberland Gap National Historical Park near the intersection of Kentucky, Tennessee, and Virginia. The tunnel consists of two separate bores which carry four lanes of traffic between Cumberland Gap, Tennessee and Middlesboro, Kentucky. It is one of only two mountain vehicular tunnels in the United States that cross a state line, the other being the East River Mountain Tunnel on Interstate 77 and U.S. Route 52 between Virginia and West Virginia. The tunnel opened to traffic in 1996 and replaced a section of highway through the Cumberland Gap that had earned the nickname "Massacre Mountain" due to its hazardous design and high rate of traffic accidents.