Gateway to the Blue Ridge Mountains
While many settlers came to the Valley from the north along the Great Wagon Road, those traveling from the east had to cross the Blue Ridge Mountains. In Augusta County, Jarman Gap was the most convenient crossing. A few miles west of the mountains where the South River threaded through the Valley became a convenient stop for travelers. What started as a roadside stop would grow into the city known as Waynesboro.
One of the first establishments was the tavern run by the Tees family — a popular stop that, according to local lore, hosted George Washington and Thomas Jefferson. The village became known as Teesville before adopting "Waynesboro" in 1797 after Revolutionary War hero Mad Anthony Wayne. Though spared much Civil War destruction, a battle fought outside the city in early 1865 marked the end of Confederate control of the Shenandoah Valley.
By the late 19th century, a planned town called "Basic City" formed on the eastern side of the South River, creating a rivalry with Waynesboro until consolidation in 1923. The 20th century brought tremendous industrial growth — the first car made in Virginia was built here. By World War II, DuPont and General Electric both operated large factories in town.
While a modern city, Waynesboro has worked hard to preserve its history. Several original 19th-century buildings downtown are listed in the National Register of Historic Places. The historic Wayne Theater has reopened as a community arts center, and Fishburne Military Academy — founded in 1879 with Gothic Revival barracks dominating the hill west of downtown — remains one of the oldest military schools in the country.
Waynesboro's proximity to the Blue Ridge Mountains puts it right in the heart of an outdoor mecca. The mountains hold Shenandoah National Park and the Blue Ridge Parkway, and Waynesboro is a popular stop for Appalachian Trail hikers. The South River flowing through town has gained national attention as a fly fishing spot, celebrated annually at the River Fest and Fly Fishing Festival.