The site now known as Buckland had long been a site of significance for trade and transportation, due to its position on Broad Run and its relationship to a network of pre-colonial Indian paths that extended north-south through several eastern states.
By the end of the eighteenth century, the village of Buckland had grown from its grain mills and quarry on Colonel Charles Carter's old Broad Run Tract to include a wool factory, church, taverns, shops, tannery, and distillery.
Samuel Love, the owner of Buckland Farm, petitioned to have the Carolina Road realigned to pass through the village in 1775. Due to the growth of trade and industry at the site, Samuel Love's son (and future Congressman) John Love had the village laid out in lots, and it was formally established as a town in 1798.
Buckland became regionally significant for helping to create the Fauquier and Alexandria Turnpike (also known as the Warrenton Turnpike), on which it was a prominent stage coach stop and post office.
The town was visited by Lafayette on his farewell tour of the U.S. in 1824 and by President Andrew Jackson numerous times. After the decline of the American grain trade in the 1820s, the rise of railroads, and increasing racial segregation, the turnpike and the town, whose inhabitants and artisans had included many free African-Americans, became less successful in the years leading up to the Civil War.
On October 19, 1863 Union cavalry under Maj. Gen. J. Kilpatrick pursued Maj. Gen. J.E.B. Stuart's cavalry along the Warrenton Turnpike but were lured into an ambush near Buckland Mills. The Federal troopers were scattered and chased five miles in an affair that came to be known as the Battle of Buckland Mills or "Buckland Races." The battle was among the Confederate cavalry's last victories of the Civil War.