16 Upcoming Races Near Winchester, VA - Matching: Trail Races

Sat, Nov 72 races

Narrow Way

Cumberland, MD

10K

Trail

View details for race Narrow Way

Schaeffer Half Marathon, 10K, 5K Trail Run

Germantown, MD

10K

Half

Trail

View details for race Schaeffer Half Marathon, 10K, 5K Trail Run

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Sat, Nov 142 races

Fall for the Park 5.5K & Flannel Fest

Manassas Park, VA

Trail

View details for race Fall for the Park 5.5K & Flannel Fest

Berryville Turkey Trot 5K & 1 Mile Kids Fun Run

Berryville, VA

1 Mile

Trail

View details for race Berryville Turkey Trot 5K & 1 Mile Kids Fun Run

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Sun, Nov 151 race

2026 Chasing Zero 5.5k (and 22k) Turkey Trot

Hamilton, VA

Trail

View details for race 2026 Chasing Zero 5.5k (and 22k) Turkey Trot

Sat, Nov 211 race

Herndon Turkey Trot 5K

Herndon, VA

Trail

View details for race Herndon Turkey Trot 5K

Sun, Nov 221 race

Fall Backyard Burn Trail Run - Riverbend

Great Falls, VA

10 Miles

Trail

View details for race Fall Backyard Burn Trail Run - Riverbend

Wed, Nov 251 race

Winery at Bull Run Turkey Trot 5k & 10k

Centreville, VA

10K

Trail

View details for race Winery at Bull Run Turkey Trot 5k & 10k

Thu, Nov 261 race

United Way of the Eastern Panhandle Turkey Trot

Martinsburg, WV

Trail

View details for race United Way of the Eastern Panhandle Turkey Trot

Fri, Nov 271 race

Black Friday 5k & 10k

Herndon, VA

10K

Trail

View details for race Black Friday 5k & 10k

Sat, Dec 51 race

Froggy Hollow 5 & 9 presented by Altra

Clarksburg, MD

Trail

View details for race Froggy Hollow 5 & 9 presented by Altra

Sun, Jan 10, 20271 race

Patriotic Pursuit 5k, 10k & Half

Williamsport, MD

Half

10K

Trail

View details for race Patriotic Pursuit 5k, 10k & Half

Sat, Mar 27, 20271 race

Vietnam Veteran's 5k

Warrenton, VA

Trail

View details for race Vietnam Veteran's 5k

Sat, May 1, 20271 race

Trail Demon 5k & 10k

Bluemont, VA

10K

Trail

View details for race Trail Demon 5k & 10k

Sat, May 15, 20271 race

SHENANDOAH SKY

Bentonville, VA

Trail

View details for race SHENANDOAH SKY

Sun, Aug 22, 20271 race

Leopold’s Preserve 5k & 10k

Broad Run, VA

10K

Trail

View details for race Leopold’s Preserve 5k & 10k

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