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When the pass through the Blue Ridge Mountains was discovered making westward expansion possible, Joseph Tees purchased a 900-acre parcel of land in 1743. When he died, his two sons divided the property between them.  William received the portion that was on both sides of the South River and the road going from Charlottesville to Staunton.  Upon the death of William, the property went to his wife and only child, Jane.  Unofficially the area was known as Teesville.  Jane married Samuel Estill and the couple bought the property rights from her mother in 1790.  Estill, in 1798, platted an area of 83 building lots with streets and alleys on both sides of the road and just west of the river.  In September 1800, 41 landowners petitioned the General Assembly to recognize the hamlet as Waynesborough, a name Estill selected in honor of General Anthony Wayne.  This was granted in January 1801 and the town was incorporated in 1834.

The town was raided by the Union Army in 1864 and, on March 2, 1865, the Battle of Waynesboro occurred.  The battle, which resulted in the defeat of General Jubal Early’s Confederate forces, was the last fought in the Shenandoah Valley.

Waynesboro was reincorporated in 1874.  In 1881, when the north-south railroad crossed the east-west line a new boomtown, Basic City, was established at that junction.

For thirty-two years Basic City and Waynesboro existed side-by-side, but ultimately consolidated under the name Waynesboro-Basic in 1923.  The following year the town was officially renamed Waynesboro and experienced a surge in industrial development that sustained economic stability through World War II.  In 1948 the town attained first-class independent city status.  Annexations at the time and in 1986 gave the City the room for expansion that is now present-day Waynesboro.

Population growth to the town was slow at first. In 1810, the town had a population of 250. By 1860, that number grew to 457. The town maintained a steady stream of visitors, however, due to its position on the Valley Turnpike, which took advantage of connections through Rockfish Gap.  The town flourished in the years that followed and gained greater access to major trading markets when the east-west railroad reached it in 1854 and the Crozet tunnel was completed through the Blue Ridge Mountains in 1858.

Some of the remaining buildings from this period of its history include the Plumb House (now a museum open for tours seasonally) and the Coiner-Quesenbury House built in 1806, believed to be the first brick house built in the town, which is still standing on Main Street.

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