The actual etymology of Shenandoah is uncertain. Native American etymologists have proposed multiple sources - Schin-han-dowi meaning River Through the Spruces, On-an-da-goa meaning River of High Mountains, an Iroquois word for Big Meadow. A widely-circulated romantic interpretation translates the name as Beautiful Daughter of the Stars; that one is almost certainly a 19th-century invention. The Skenandoa theory is the most touching but cannot be confirmed. Other accounts trace the name to an Iroquoian chief named Sherando defeated by the Powhatan ruler Opechancanough, whose son's followers later became the Shawnee. The various theories share one thing: an Indigenous origin filtered through generations of Anglo-American mishearing. The valley's most famous word is one no one is quite sure how to translate.

The Shenandoah Valley is a 200-mile-long geographic trough running from the Potomac River in the north to the James River in the south, bounded east by the Blue Ridge and west by the eastern front of the Ridge-and-Valley Appalachians. Massanutten Mountain runs through the central section, splitting the valley floor in two. The valley physiographically belongs to the Great Appalachian Valley, the immense north-south trough that extends from Quebec south through the Carolinas. It encompasses eight Virginia counties and two in West Virginia. The cultural region extends further, picking up Roanoke and the Virginia Highlands. Ten independent cities cluster within or near the valley: Winchester, Harrisonburg, Staunton, Waynesboro, Lexington, Buena Vista, Covington, Roanoke, Salem, and Front Royal.

By the mid-19th century, the Shenandoah Valley was producing wheat, corn, livestock, and fruit in quantities that made it strategically vital to the Confederacy. The breadbasket of the Confederacy fed Robert E. Lee's army. Three major Civil War campaigns turned the valley into a contested zone. Stonewall Jackson's 1862 Valley Campaign defeated three Union armies in succession through speed, surprise, and intimate knowledge of the terrain. In summer 1864, Jubal Early cleared the Valley of Union forces and rode his army to the outskirts of Washington itself. Then Philip Sheridan was sent to end the threat permanently. Sheridan's autumn 1864 campaign - which he called the Burning - applied scorched-earth tactics to the valley. His troops burned barns, mills, and crops, leaving 2,000 burned barns behind and a region whose agricultural infrastructure took decades to rebuild. The phrase the Burning is still used here.

Below the cultivated topsoil of the valley lies a stack of cultural layers. Before European contact, Shawnee, Tuscarora, Iroquois, Catawba, and others used the valley as a war road and shared hunting ground; few permanent settlements survive in the archaeological record because the valley was mostly through-territory for warring nations. In the 1720s and 30s, Quakers and Mennonites came south from Pennsylvania, followed by Germans (Shenandoah Deitsch) and Scots-Irish in larger numbers. The first permanent European settler was the German Adam Miller, in 1727. By the 1740s the Iroquois had sold their claims to the valley to Virginia for 200 pounds in gold at the Treaty of Lancaster. The Great Wagon Road - originally an Indigenous warriors' trail - became the Valley Pike, then U.S. Route 11, then Interstate 81. The valley today still carries the marks of every group that passed through. Mennonite farms, Black Baptist churches, Latino immigrant communities working the poultry plants, Civil War battlefields, German place names, Oneida memories - all of them present, none entirely settled.