The Ashby’s Gap Turnpike GeoTrail
Middleburg
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 cache is not at the posted coordinates! They will lead you to a convenient parking lot for your exploration.
According to tradition, the town of Middleburg takes its name from the position it occupies roughly between Alexandria and Winchester. By the middle of the 18th century a handful of structures existed along the road to Ashby’s Gap, but the town wasn’t formally established until 1787. In that year, Revolutionary War veteran Leven Powell purchased a number of acres and began laying out lots for development.
In the decades before the Civil War, Middleburg grew into a prosperous market town along the Ashby’s Gap Turnpike. Crops and livestock moved from nearby plantations east to Alexandria, while settlers moved westward towards Winchester and points beyond. Coffles of enslaved African-Americans also moved along the turnpike, to be sold to plantations in the Deep South as local planters switched from tobacco to less labor-intensive crops like wheat.
When the issue of secession was raised in the spring of 1861, the voters of Middleburg chose unanimously to leave the United States, and many local men marched off to war. Those that remained behind were caught up in a vicious guerrilla war between Confederate partisans and the US Army. Middleburg gained a reputation as the unofficial capital of “Mosby’s Confederacy,” a region where Confederate raider John S. Mosby and his men operated. Many Middleburg citizens supported Mosby and his men by providing intelligence, supplies, and hiding places.
By the beginning of the 20th century, a new group of settlers came to live in and around Middleburg. Wealthy businessmen and women from the northeast states began moving to the area, drawn by the beautiful landscape. Middleburg quickly became the heart of the Virginia hunt country, and the town’s equestrian heritage is on clear display. The elite social scene that developed around the hunt country drew in many celebrities in the early and mid-20th century. Among the most famous were President and Mrs. John F. Kennedy, who built a country home south of town in 1962.
With any luck you might bump into a celebrity as you search the streets of Middleburg for the clues you need to locate the cache. To find the final coordinates you must answer the following questions. All of the answers can be found by looking on Washington or North Madison Street, no further east than Jay Street and no further west than The Plains Road. You do not need to enter any buildings.
A = In what year was a pavilion dedicated to Jackie Onassis? 199A
B = What year was the Middleburg United Methodist Church built (according to the plaque)? 185B
C = What number Rhode Island Cavalry Regiment fought in the Battle of Middleburg?
D = In what year does the Red Fox Inn claim to have been established? 1D28
E = How many casualties did Robertson’s Brigade suffer in the battle here? E5
F = What year was Emmanuel Episcopal Church founded? 18F2
G = When year was the Middleburg Community Center built? 19G8
H = In what year was the Middleburg Fox Statue dedicated? 20H9
I = How many regiments under General Gregg participated in the Battle? I
J = What year does the current Middleburg Baptist Church congregation date to (the church is not on Washington Street, but you will see a sign)? 18J7
The cache is located at N 38° AB.CDE W 77° FG.HIJ
Checksum is 42.
VPHA has permission from the landowner. Please seek the final stage during daylight hours only.
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.