"[7] In 1787, Nathaniel Gordon purchased 1,350 acres (5.46 square km) of land, then known as "Newville," from a cousin of President James Madison.

In 1794, or perhaps earlier, Gordon applied for and was granted a license to operate a tavern there, which, as was typical of the time, was used as a place to eat, lodge and discuss local matters.

President Thomas Jefferson described the tavern in 1802 as a "good house" when recommending the best route south to Charlottesville from the recently established national capital on the Potomac.

At the time of Gordon's death in 1820, Gordonsville had, in addition to the tavern, a post office, several homes, a general mercantile store and a blacksmith shop.

The later division and sale of lots from this property, and the construction of adjacent roads, would foster growth of the town up to and during the Civil War.

In 1854, the Orange & Alexandria Railroad completed its line into Gordonsville, connecting the area with northern portion of Virginia.

During the war years, Robert E. Lee, James Longstreet, Stonewall Jackson, Richard S. Ewell and A. P. Hill spent time in Gordonsville.

Major Gen. Philip Sheridan led a raid in the direction of Gordonsville and Charlottesville but was stopped by Wade Hampton's Confederate cavalry in the vicinity of Trevilian Station.

The Civil War ended in 1865 and with Gordonsville being largely unscathed, passenger rail service was quickly reestablished.

In the following years it was "a flourishing and fast improving town" and its prosperity gave rise to then-superior educational facilities and fine examples of period architecture, many of which are still standing on N. Main and W. Baker Streets.

Gordonsville had the unique reputation as a fast-food emporium in the 1870s, with an active market of food vendors serving rail travelers as they stopped in the town.

[7] As alternative rail lines and roads were constructed bypassing Gordonsville, it morphed into a quiet, rural market town.

[8] In the early 1970s, following the 100-year anniversary of the town's incorporation, a nonprofit organization named Historic Gordonsville Inc. was formed.

[13] The historic district and the Exchange Hotel are both within the town limits of Gordonsville; Black Meadow and Rocklands are nearby.