Middleburg Gravel 50K is a 29.5-mile loop starting in Middleburg, with 1,716 feet of climbing. About 11.2 miles (38%) are on gravel or dirt roads and 18.3 miles are paved. The longest unpaved stretch runs 5.5 miles on Woodtrail Road, Unison Road near Airmont and Unison.
Route snapshot
What to expect
This loop spreads its gravel evenly across the ride: 5.2 gravel miles in the first half and 6.0 in the second. Along the way it links Saint Louis, Philomont, Flint Hill, Airmont and Unison.
The course tops out at 623 feet around mile 13.9 and drops as low as 318 feet. Expect 8 climbs of 80 feet or more; the biggest gains 204 feet over 0.9 miles starting near mile 27.0. The steepest quarter-mile averages about 7.8% near mile 23.0. At roughly 58 feet of climbing per mile, we rate it intermediate.
- 5.5 miles of continuous gravel on Woodtrail Road and Unison Road near Airmont and Unison.
- More unpaved stretches on Snake Hill Road and Greggsville Road.
- 38% of the distance is on gravel or dirt.
- Paved connectors include Duffey Lane, Beaverdam Bridge Road, North Fork Road, Black Oak Road and Newlin Mill Road.
- A steep pitch of about 7.8% near mile 23.0. Choose gears that let you stay seated on loose gravel.
- Carry water, a spare tube and a plug kit.
Ride notes. Start and finish in Middleburg. These are working farm roads shared with horses, tractors and local traffic: slow down and pass wide around horses, and see VeloSafe for more. Gravel changes with the weather, so expect loose stone after a fresh grading and soft spots after heavy rain. Spring and fall are our favorite seasons out here.

Elevation and surface

Gravel sections
Unpaved stretches of half a mile or more, in riding order:
- Mile 2.8–6.3 (3.5 mi): Snake Hill Road, Pot House Road, Mountville Road — near Saint Louis
- Mile 9.5–10.4 (0.9 mi): Greggsville Road — near Philomont
- Mile 11.5–12.2 (0.7 mi): Colchester Road — near Flint Hill
- Mile 16.2–21.7 (5.5 mi): Woodtrail Road, Unison Road — near Airmont and Unison
- Mile 26.0–26.7 (0.7 mi): Snake Hill Road — near Saint Louis
Photos from the route


Photos taken along this route on our rides.
Get the route
Surface data comes from Ride with GPS. Road names come from OpenStreetMap. Gravel roads change with weather and maintenance, so check conditions before you ride and follow our VeloSafe guidance on rural roads.
