From the streets of modern-day Leesburg, VA, riders motor through the idyllic horse and vineyard country of historic Loudoun and Fauquier counties, VA, and also will navigate briefly into Maryland and West Virginia. This backroad ramble can be taken anytime from spring through fall but is most enjoyable during fall colors in mid-October.
Approximately 156 miles
Starbucks, 531 E Market St, Leesburg, VA
Hunter's Head Tavern, 9048 John S. Mosby Hwy, Upperville, VA, (540) 592-9020. Hunter's Head Tavern is an authentic English pub, preparing dishes using local, organic meat and produce and serving homemade desserts.
Scenery (4 out of 5)
Pastoral landscapes, cool mountain breezes, expansive vistas, charming back-in-time villages, verdant valleys, and off-the-beaten-path byways are a feast for the senses.
Traffic (4 out of 5)
Moderate to light traffic is the norm, except on brief sections of US-50 and US-15, which are main thoroughfares through the area.
Difficulty (3 out of 5)
The route consists mostly of sweeping curves and frequent elevation changes. The most technically challenging road is Chestnut Hill Road, where it ascends the Blue Ridge Mountains in West Virginia.
Road Conditions (3 out of 5)
Although generally in good shape, road conditions vary on the more rural portions of the route; there are a couple of short sections, though, with some potholes.
Points of Interest
Bluemont, VA (formerly Snickersville)
Settlement in this micro-village, located at the foot of the Blue Ridge Mountains, began in the 1770s.
Mount Weather Emergency Assistance Center
Above ground is FEMA's National Emergency Coordinating Center, but there's also rumored to be an extensive underground complex to house or replace the American government in the event of a major catastrophe.
Sky Meadows State Park
This 1,864-acre historic farm park has panoramic views of rolling pastures and lush woodlands and offers nature and history programs year-round.
Historic Middleburg, VA
Middleburg, which is the unofficial capital of Northern Virginia's horse country, traces its history back to the late 18th century.
Aldie Mill Historic Park
The restored mill is an impressive four-story brick building with tandem metal overshot waterwheels, which recalls an era when gristmills served as a vital center of communities.