Choose Your Quest
Three paths diverge on the W&OD Trail. Each forged for a different breed of warrior. All starting from Herndon, Virginia.
The W&OD Trail — Your Battleground
30
Miles
The Squire
A noble beginning. Ride 30 miles out and back on the W&OD Trail from Herndon west to Foxridge Park in Leesburg, then retrace your path home. Perfect for those new to the fellowship or seeking a spirited challenge.
Terrain
Flat, fully paved trail through Northern Virginia countryside
Turnaround
Foxridge Park, Leesburg
Elevation
~300 ft gain
50
Miles
The Knight
Prove your valor. 50 miles of steel and determination along the W&OD. From Herndon, ride west through rolling hills and historic towns all the way to the trail's western terminus in Purcellville, then retrace the path back to Herndon.
Terrain
Flat to rolling, fully paved with some gentle grades west of Leesburg
Turnaround
Purcellville — W&OD western terminus
Elevation
~800 ft gain
100
Miles
The Legend
Only the mightiest dare attempt The Legend. 100 miles of pure conquest. From Herndon, ride east to the W&OD terminus in Alexandria, continue via the Four Mile Run Trail to downtown Alexandria, then retrace north and ride the full W&OD west to Purcellville before returning to Herndon.
Terrain
Full W&OD Trail + Four Mile Run Trail, all paved
Turnaround
Downtown Alexandria → Purcellville
Elevation
~1,500 ft gain
Ready to forge your legacy?
Join the Ride