The Ashby’s Gap Turnpike GeoTrail
Upperville
Presented by the Virginia Piedmont Heritage Area
This cache is part of a series that takes you along the former Ashby’s Gap Turnpike. For centuries, this path was a vital thoroughfare across Northern Virginia. From its beginnings as a Native American trail, through its use as a colonial road and 19th century turnpike, to its transformation into a modern highway, this road has seen a lot of history. The Virginia Piedmont Heritage Area invites you to follow in the footsteps of Native hunters, colonial settlers, enslaved African-Americans, Civil War soldiers, and more.
The village of Upperville was established in the 1790s, when it was known as Carrstown, after early settler Josephus Carr. Like Middleburg, the town thrived on the traffic brought by the Turnpike, and wheat and other products from the surrounding plantations used the road network to reach local mills and far-off markets. The area was also renowned for its horses, in large part due to Colonel Richard Dulany. Dulany was responsible for establishing the Upperville Colt and Horse Show in the 1850s, and it is the longest running show of its kind in the United States. If you visit in early June be prepared for serious traffic along the old Turnpike!
Equestrian sports continued to draw people to Upperville throughout the late 19th and early 20th centuries. Prominent families bought up many of the old plantation estates and transformed them into stud farms, polo centers, and other equestrian facilities. One such farm is nearby Llangollen, which was bought in 1930 by John Hay Whitney. “Jock” as he was known, was a prominent businessman who was deeply involved in the film industry, and among his most notable projects was partially funding the production of Gone with the Wind. Many stars of Hollywood’s golden age would visit the Whitneys in Upperville. The famous philanthropist Paul Mellon was also drawn to Upperville, and spent much of his later life at Rokeby Farm east of town. Trinity Church, which dominates the center of town, was a gift of the Mellons to the community in the 1960s.
Another Upperville landmark is Buchanan Hall, located on the very east end of town next to the community park. Built in the 1920s as a private wedding venue, it has since become a fixture of Upperville’s social life. In its early years, the Hall played host to a local jazz musician named Chauncy Brown. He was often accompanied by an up-and-coming musician from Washington DC named Duke Ellington. Legend also has it that the jazz classic “Sweet Georgia Brown” may have been inspired by Chauncy’s wife. Decades later, a teenaged girl from nearby Winchester wowed audiences with her powerful voice. Virginia Hensley would go on to achieve international fame as Patsy Cline.
The town of Upperville has also been immortalized in poetry. John Updike penned the following verse in 1961, entitled “Upon Learning That A Town Exists In Virginia Called Upperville”
In Upperville, the upper crust
Say “Bottoms up!” from dawn to dusk
And “Ups-a-daisy, dear!” at will—
I want to live in Upperville
One-upmanship is there the rule
And children learn about, at school,
“The Rise of Silas Lapham” and
Why gravitation has been banned.
High hamlet, ho!—my mind’s eye sees
Thy ruddy uplands, lofty trees,
Upsurging streams, and towering dogs;
There are no valleys, dumps, or bogs.
Depression never dares intrude
Upon thy sweet upswinging mood;
Downcast, long-fallen, let me go
To where the cattle never low.
I’ve always known there was a town
Just right for me; I’ll settle down
And be uplifted all day long—
Fair Upperville, accept my song.
Please seek the cache during daylight hours only. This cache is placed with the permission of Fauquier County Parks.
VPHA’s mission is to educate and advocate for the preservation of the extraordinary historic landscape and culture of the Virginia Piedmont Heritage Area for future generations. The Area includes all or parts of five counties in the northern Virginia Piedmont and lower Shenandoah Valley: Loudoun, Fauquier, Clarke, Prince William, and Warren Counties.
By telling our stories, we hope to inspire people to care for and protect our outstanding historical resources.