Nathaniel Gordon purchased Template:Convert in 1787 and in 1794, or possibly earlier, applied for and was granted a license to operate a tavern. Travelers leaving the Charlottesville of Thomas Jefferson's day followed the "Fredericksburgh Great road" northward which, at the site of the present traffic circle in Gordonsville, crossed the road from Richmond leading west over the Blue Ridge Mountains into the Valley. President Jefferson described Gordon’s in 1802 as a "good house" when recommending the best route south to Charlottesville from the recently established National capital on the Potomac.
The building was known as Gordon’s Tavern, Gordon Tavern or later as Gordon Inn. Stagecoach passengers found a well-furnished public house where they could refresh themselves with apple brandy -'the common drink of the country,' a visiting Englishman noted, or other spirits. The commemorative marker at the site lists these prominent Americans as guests at the tavern: George Washington, Thomas Jefferson, James Monroe, James & Philip Pendleton Barbour, James Waddel, William Wirt & Henry Clay. Another famous visitor was Major General the Marquis de Lafayette.
In 1839, the General Assembly authorized the Louisa Rail Road Company to extend its line from Louisa Court House to Gordonsville. Thus was ushered in a time of growth and prosperity for Gordonsville. It became a center of trade for the plantations and farms in the surrounding countryside. The Orange & Alexandria railroad completed its line into Gordonsville in 1854. The wood-burning locomotives traveled at speeds of up to twenty miles per hour.
Gordonsville and the railroads which intersected there were of vital importance to the Confederacy. Troops from Richmond on the way to the battle of Bull Run on July 21, 1861 came through town. During the war years, Robert E. Lee, James Longstreet, Stonewall Jackson, Ewell & 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. Gordonsville was threatened many times but was always successfully defended by the Confederates.