Upperville Friday Gravel 38K is a 23.6-mile loop starting in Upperville, with 1,598 feet of climbing. About 17.5 miles (74%) are on gravel or dirt roads and 6.1 miles are paved. The longest unpaved stretch runs 7.7 miles on Yellow Schoolhouse Road, Foggy Bottom Road, Ridgeside Road, Trappe Road near Paxson.
Route snapshot
What to expect
This loop spreads its gravel evenly across the ride: 9.8 gravel miles in the first half and 7.7 in the second. Along the way it links Saint Louis, Unison, Airmont and Paxson.
The course tops out at 716 feet around mile 16.8 and drops as low as 362 feet. Expect 6 climbs of 80 feet or more; the biggest gains 209 feet over 3.2 miles starting near mile 13.7. The steepest quarter-mile averages about 7.3% near mile 1.6. At roughly 68 feet of climbing per mile, we rate it beginner-friendly.
- 7.7 miles of continuous gravel on Yellow Schoolhouse Road, Foggy Bottom Road, Ridgeside Road and Trappe Road near Paxson.
- More unpaved stretches on Welbourne Road and Greengarden Road.
- 74% of the distance is on gravel or dirt.
- Paved sections on John S Mosby Highway and Snickersville Turnpike, busier roads. Ride single file and stay alert.
- Paved connectors include Millville Road.
- A steep pitch of about 7.3% near mile 1.6. 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 Upperville. 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 0.6–2.8 (2.2 mi): Greengarden Road
- Mile 4.0–11.6 (7.6 mi): Welbourne Road, Quaker Lane, Unison Road, Woodtrail Road — near Saint Louis and Unison and Airmont
- Mile 12.8–20.5 (7.7 mi): Yellow Schoolhouse Road, Foggy Bottom Road, Ridgeside Road, Trappe Road — near Paxson
Photos from the route
Photos taken along this route on our rides.
Get the route
Surface data comes from Strava. 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.
