Gordonsville grew up around a tavern established by Nathaniel Gordon in 1794, where the circle is today. After the railroad arrived in 1840, development began around the rail depot at the other end of town. By the 1850s they were filling in the gap, which is Main Street Gordonsville today.
Gordon first settled the area when he purchased a plantation “at the foot of the southwest mountains” in Orange County in 1787. Later, he opened a popular tavern which hosted Thomas Jefferson, James Madison and Major General the Marquis de Lafayette, among other famous figures of early America. Jefferson told southern legislators it was a “good house” for stopping over on their way to Congress. The community became officially known as “Gordonsville” in 1813 when Gordon was appointed the first postmaster of the area surrounding his tavern.
Meanwhile, Gordonsville was a significant economic hub in the 19th century, becoming the center of trade in Orange County. It was a railroad junction with the north/south tracks of what was then the Orange & Alexandria, (today’s CSX) and the east/west Virginia Central, connecting Richmond to Staunton. Also, two major roads connected Gordonsville to the breadbasket of the Confederacy, the Shenandoah Valley. Those roads today are Rt. 33, the Rockingham Turnpike to Swift Run Gap and Rt. 231, the Blue Ridge Turnpike. The convergence of those historic routes with Route 15, at the traffic circle, position Gordonsville on the way to Virginia destinations in every direction.
Gordonsville was a critical crossroads in the Civil War, as key supply lines funneled through town by rail and road. The Federals tried on several occasions to capture this town, without success. They came close…to the top of Cameron’s (Bell’s) Mountain, but they never took the town. Gordonsville also was home to the Exchange Hotel Civil War Receiving Hospital, treating more than 23,000 sick and wounded between June 1, 1863 and May 5, 1864. By war's end over 70,000 men had been treated at the Gordonsville Receiving Hospital. The Exchange Hotel has been refurbished and is now a wonderful museum.
Following the Civil War, Gordonsville remained a hub of activity, as travelers passed through town by road and rail. Train passengers were treated to traditional southern fare of biscuits and chicken by the town’s enterprising African-American women who balanced their tasty treats on platters atop their heads for hungry train travelers. Gordonsville later became know as the "fried chicken capital of the universe". Main Street teemed with commerce until the town’s devastating fire in 1916. When a new rail line in Barboursville reduced train traffic through town, Gordonsville gave up its mantle as the county commercial center.
Like most small towns in America, Gordonsville is a Main Street community with commerce and social activities centered on its primary street. Churches, homes and businesses flank the tree-lined street giving Gordonsville a decidedly southern flair, rich with hospitality and charm. Today, Gordonsville’s Main Street is enjoying a commercial revival with boutique shops and restaurants making the town a destination once again.