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Upcoming Races Near Winchester, VA - Matching: Trail Races

Froggy Hollow 5 & 9 presented by Altra

Clarksburg, MD

Saturday, March 28th, 2026

Featured

Trail

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

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Southern Fauquier Ruritan 5K Run/ Walk

Midland, VA

Saturday, April 11th, 2026

5K

Trail

View details for race Southern Fauquier Ruritan 5K Run/ Walk

Spring Backyard Burn Trail Run - Lake Fairfax

Reston, VA

Sunday, April 19th, 2026

Trail

View details for race Spring Backyard Burn Trail Run - Lake Fairfax

Run the Rock | Leesburg

Ashburn, VA

Saturday, April 25th, 2026

5K

Trail

View details for race Run the Rock | Leesburg

Courage Day 5K

Purcellville, VA

Sunday, April 26th, 2026

5K

Trail

View details for race Courage Day 5K

2025 Girls on the Run Spring 5K - Frederick County

Frederick, MD

Sunday, May 31st, 2026

5K

Trail

View details for race 2025 Girls on the Run Spring 5K - Frederick County

FSRC Independence 5000

Frederick, MD

Saturday, July 4th, 2026

5K

Trail

View details for race FSRC Independence 5000

Run At The Top Summer Youth Running Camp

Stephens City, VA

Monday, July 20th, 2026

Trail

View details for race Run At The Top Summer Youth Running Camp

Blue Crab Bolt Trail Run - Schaeffer Farms

Germantown, MD

Saturday, July 25th, 2026

5K

Trail

Fast

View details for race Blue Crab Bolt Trail Run - Schaeffer Farms

SHENANDOAH VALLEY RUNNERS Presents SPEAR TRAIL ...

Stephens City, VA

Saturday, July 25th, 2026

5K

10K

Ultra

Trail

View details for race SHENANDOAH VALLEY RUNNERS Presents SPEAR TRAIL SERIES

Blue Crab Bolt Trail Run - Little Bennett

Clarksburg, MD

Saturday, August 1st, 2026

10K

Trail

View details for race Blue Crab Bolt Trail Run - Little Bennett

Othello Park Labor Day 1K/5k

Knoxville, MD

Monday, September 7th, 2026

5K

Trail

View details for race Othello Park Labor Day 1K/5k

The Final Countdown - Tribute

Martinsburg, WV

Saturday, September 19th, 2026

Trail

Fast

View details for race The Final Countdown - Tribute

Trails 4 Miles

Stephens City, VA

Saturday, September 26th, 2026

1 Mile

Trail

View details for race Trails 4 Miles

River's Edge Endurance Challenge

Brunswick, MD

Saturday, September 26th, 2026

5K

Trail

View details for race River's Edge Endurance Challenge

Runnin' with the Dogs 5K

Martinsburg, WV

Saturday, September 26th, 2026

5K

Trail

View details for race Runnin' with the Dogs 5K

Rocky Gap 25K, 50K, Relay Trail Run

Flintstone, MD

Sunday, October 11th, 2026

1 Mile

Trail

View details for race Rocky Gap 25K, 50K, Relay Trail Run

Buzz Sawyer Western Maryland Marathon/Half Mara...

Hancock, MD

Sunday, October 18th, 2026

Marathon

Half

10K

Trail

View details for race Buzz Sawyer Western Maryland Marathon/Half Marathon/10k

Fall Backyard Burn Trail Run - Lake Fairfax

Reston, VA

Sunday, October 18th, 2026

1 Mile

10 Miles

Trail

View details for race Fall Backyard Burn Trail Run - Lake Fairfax

Schaeffer Half Marathon, 10K, 5K Trail Run

Germantown, MD

Saturday, November 7th, 2026

5K

10K

Half

Trail

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

Fall Backyard Burn Trail Run - Riverbend

Great Falls, VA

Sunday, November 22nd, 2026

10 Miles

Trail

View details for race Fall Backyard Burn Trail Run - Riverbend

Explore more in Winchester, VA

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

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