Upperville Zig-Zag Gravel

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Rodrigo Loureiro

November 2, 2026

Upperville Zig-Zag Gravel is a 42.0-mile loop starting in Upperville, with 2,428 feet of climbing. About 31.9 miles (76%) are on gravel or dirt roads and 10.1 miles are paved. The longest unpaved stretch runs 8.4 miles on Ebenezer Church Road, Yellow Schoolhouse Road, Foggy Bottom Road, Austin Grove Road, Ridgeside Road, Trappe Road near Airmont and Paxson.

Route snapshot

Distance

42.0 mi

Climbing

2,428 ft

Surface

76% gravel · 24% paved

Difficulty

●●○ Intermediate

Route type

Loop

Start

Upperville

High point

712 ft

Riding time

3:00–4:15 h

What to expect

This loop spreads its gravel evenly across the ride: 14.8 gravel miles in the first half and 17.1 in the second. Along the way it links Paxson, Bluemont, Silcott Spring and Airmont.

The course tops out at 712 feet around mile 9.6 and drops as low as 421 feet. Expect 11 climbs of 80 feet or more; the biggest gains 187 feet over 3.3 miles starting near mile 5.3. The steepest quarter-mile averages about 8.5% near mile 21.3. At roughly 58 feet of climbing per mile, we rate it intermediate.

Highs

8.4 miles of continuous gravel on Ebenezer Church Road, Yellow Schoolhouse Road, Foggy Bottom Road and Austin Grove Road near Airmont and Paxson.
More unpaved stretches on Trappe Road and Paxson Road.
76% of the distance is on gravel or dirt.

Heads-up

Paved sections on Leesburg Pike, Snickersville Turnpike and John S Mosby Highway, busier roads. Ride single file and stay alert.
Paved connectors include Trappe Road, Llangollen Road, Foggy Bottom Road, Airmont Road and Greengarden Road.
A steep pitch of about 8.5% near mile 21.3. Choose gears that let you stay seated on loose gravel.
At 42.0 miles, plan your water and food before you leave Upperville.

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.

Upperville Zig-Zag Gravel route map, gravel sections in orange and paved in gray — Route map: gravel and unpaved sections in orange, paved roads in gray. Green dot marks the start.

42.0 mi2,428 ft climbing31.9 mi gravel10.1 mi paved

Elevation and surface

Elevation profile, shaded by surface: orange is gravel or dirt, gray is paved.

Gravel sections

Unpaved stretches of half a mile or more, in riding order:

Mile 1.3–2.9 (1.6 mi): Llangollen Road
Mile 5.9–12.4 (6.5 mi): Trappe Road, Ridgeside Road, Foggy Bottom Road — near Paxson
Mile 14.0–15.6 (1.6 mi): Calumet Lane — near Bluemont
Mile 16.0–18.3 (2.3 mi): Yellow Schoolhouse Road — near Paxson
Mile 18.6–23.3 (4.7 mi): Paxson Road, Black Oak Road — near Silcott Spring
Mile 24.1–27.7 (3.6 mi): Woodtrail Road, Poor House Road — near Airmont
Mile 28.2–36.6 (8.4 mi): Ebenezer Church Road, Yellow Schoolhouse Road, Foggy Bottom Road, Austin Grove Road, Ridgeside Road, Trappe Road — near Airmont and Paxson
Mile 39.0–41.1 (2.1 mi): Greengarden Road

Photos from the route

Gravel road and countryside on the Upperville Zig-Zag Gravel route

Photos taken along this route on our rides.

Get the route

Open on Ride with GPS

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.

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