Upcoming Races Near Winchester, VA in May, 2026

Name: 2026 Girls on the Run Spring 5K - Frederick County
Start: 2026-05-31
End: 2026-05-31
Location: Frederick

Apple Blossom Valley Health 10K and Shenandoah ...

Winchester, VA

Friday, May 1st, 2026

Featured

1 Mile

10K

View details for race Apple Blossom Valley Health 10K and Shenandoah Valley Orthodontics Kids' Bloomin' Mile

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LifeSpring Pregnancy Centers 5K Race

Culpeper, VA

Saturday, May 2nd, 2026

View details for race LifeSpring Pregnancy Centers 5K Race

Loudoun Serenity House - 5K Run/Walk for Recovery

Leesburg, VA

Saturday, May 2nd, 2026

View details for race Loudoun Serenity House - 5K Run/Walk for Recovery

2026 Frederick Running Festival with Girls on t...

Frederick, MD

Saturday, May 2nd, 2026

1 Mile

View details for race 2026 Frederick Running Festival with Girls on the Run

Flip N Cheer Booster Club 5Kake Fun Run/Walk

Harpers Ferry, WV

Saturday, May 2nd, 2026

View details for race Flip N Cheer Booster Club 5Kake Fun Run/Walk

Frederick Running Festival

Frederick, MD

Saturday, May 2nd, 2026

Half

View details for race Frederick Running Festival

Ashburn Village Fiesta 5K/10K/Fun Run

Ashburn, VA

Saturday, May 2nd, 2026

10K

View details for race Ashburn Village Fiesta 5K/10K/Fun Run

Cougar Literacy Run

Manassas Park, VA

Saturday, May 2nd, 2026

View details for race Cougar Literacy Run

Run The Greenway

Ashburn, VA

Sunday, May 3rd, 2026

10K

View details for race Run The Greenway

BRRC Spring 2026 Long Run/Half Marathon Trainin...

Frederick, MD

Sunday, May 3rd, 2026

Half

View details for race BRRC Spring 2026 Long Run/Half Marathon Training Group

Tiki Trot 5K, Beer Mile & Tiki-tizer Mile

Williamsport, MD

Saturday, May 9th, 2026

1 Mile

View details for race Tiki Trot 5K, Beer Mile & Tiki-tizer Mile

Shenanduro

Bentonville, VA

Saturday, May 9th, 2026

Fast

View details for race Shenanduro

The Bettie Jane Cancer Foundation 5K Run/Walk

Frederick, MD

Saturday, May 9th, 2026

View details for race The Bettie Jane Cancer Foundation 5K Run/Walk

Historic Waterford Trail Run/Walk

Waterford, VA

Saturday, May 9th, 2026

10K

View details for race Historic Waterford Trail Run/Walk

Move for Mental Health

Warrenton, VA

Saturday, May 9th, 2026

View details for race Move for Mental Health

=PR= Races: Devotion to Children Mother's Day 4...

Reston, VA

Sunday, May 10th, 2026

1 Mile

View details for race =PR= Races: Devotion to Children Mother's Day 4 Miler

Front Royal Kiwanis 5K

Front Royal, VA

Saturday, May 16th, 2026

View details for race Front Royal Kiwanis 5K

Luray Police Foundation 5K - 2026

Luray, VA

Saturday, May 16th, 2026

View details for race Luray Police Foundation 5K - 2026

Harpers Ferry Half Marathon & 5K

Harpers Ferry, WV

Saturday, May 16th, 2026

Half

View details for race Harpers Ferry Half Marathon & 5K

7th Annual Farm 5K Benefit Run/Walk at Wardensv...

Wardensville, WV

Saturday, May 23rd, 2026

View details for race 7th Annual Farm 5K Benefit Run/Walk at Wardensville Garden Market

Gainesville High School Cardinal 5K Run/Walk

Gainesville, VA

Saturday, May 23rd, 2026

View details for race Gainesville High School Cardinal 5K Run/Walk

Amani Brewing 5K & Beer Mile

Martinsburg, WV

Saturday, May 23rd, 2026

1 Mile

View details for race Amani Brewing 5K & Beer Mile

A SALUTE TO OUR TROOPS

Ashburn, VA

Monday, May 25th, 2026

View details for race A SALUTE TO OUR TROOPS

39th Annual Loudoun Street Mile

Winchester, VA

Monday, May 25th, 2026

1 Mile

View details for race 39th Annual Loudoun Street Mile

May 25th, Hamilton Day Mighty Miler

Hamilton, VA

Monday, May 25th, 2026

1 Mile

View details for race May 25th, Hamilton Day Mighty Miler

Ringing in Hope: A Salute to our Troops

Ashburn, VA

Monday, May 25th, 2026

10K

View details for race Ringing in Hope: A Salute to our Troops

Panda 5K & 1K Fun Run

Frederick, MD

Monday, May 25th, 2026

View details for race Panda 5K & 1K Fun Run

Virginia Wine Country Half Marathon 2026

Hillsboro, VA

Saturday, May 30th, 2026

Half

10K

View details for race Virginia Wine Country Half Marathon 2026

Lyme Warrior's Run Like A Warrior 5ks - Frederi...

Frederick, MD

Saturday, May 30th, 2026

View details for race Lyme Warrior's Run Like A Warrior 5ks - Frederick, MD

MomFuel 5K

Sterling, VA

Saturday, May 30th, 2026

View details for race MomFuel 5K

2026 Girls on the Run Spring 5K - Washington Co...

Hagerstown, MD

Saturday, May 30th, 2026

View details for race 2026 Girls on the Run Spring 5K - Washington County

Culpeper Law Enforcement Torch Run Run/Walk

Culpeper, VA

Saturday, May 30th, 2026

View details for race Culpeper Law Enforcement Torch Run Run/Walk

MCRRC Little Bennett 10K

Clarksburg, MD

Saturday, May 30th, 2026

10K

View details for race MCRRC Little Bennett 10K

2026 Girls on the Run Spring 5K - Frederick County

Frederick, MD

Sunday, May 31st, 2026

View details for race 2026 Girls on the Run Spring 5K - Frederick County

Explore more in Winchester, VA

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Virginia races

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