Upcoming 5K Races Near Winchester, VA

Name: Chrysalis Vineyards Wine Run 5k
Start: 2026-08-22
End: 2026-08-22
Location: Middleburg

Cougar Literacy Run

Manassas Park, VA

Saturday, May 2nd, 2026

Featured

View details for race Cougar Literacy Run

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LifeSpring Pregnancy Centers 5K Race

Culpeper, VA

Saturday, May 2nd, 2026

View details for race LifeSpring Pregnancy Centers 5K Race

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

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

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

Frederick Running Festival

Frederick, MD

Saturday, May 2nd, 2026

Half

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Run The Greenway

Ashburn, VA

Sunday, May 3rd, 2026

10K

View details for race Run The Greenway

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

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

Strasburg Mayfest 5K to Benefit Abigail's Journey

Strasburg, VA

Saturday, May 9th, 2026

View details for race Strasburg Mayfest 5K to Benefit Abigail's Journey

5k Neon Run and 1-Mile Fun Run/Walk presented b...

Greencastle, PA

Friday, May 15th, 2026

1 Mile

View details for race 5k Neon Run and 1-Mile Fun Run/Walk presented by Relay For Life of Franklin & Fulton Counties

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

Amani Brewing 5K & Beer Mile

Martinsburg, WV

Saturday, May 23rd, 2026

1 Mile

View details for race Amani Brewing 5K & Beer Mile

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

Panda 5K & 1K Fun Run

Frederick, MD

Monday, May 25th, 2026

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

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

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

Frederick, 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

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

Virginia Wine Country Half Marathon 2026

Hillsboro, VA

Saturday, May 30th, 2026

Half

10K

View details for race Virginia Wine Country Half Marathon 2026

MomFuel 5K

Sterling, VA

Saturday, May 30th, 2026

View details for race MomFuel 5K

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

2025 Girls on the Run Spring 5K - Frederick County

Frederick, MD

Sunday, May 31st, 2026

Trail

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

Love, KK - Annual 5KK Race

Leesburg, VA

Saturday, June 6th, 2026

View details for race Love, KK - Annual 5KK Race

Navy Federal Credit Union 5K- Winchester

Winchester, VA

Saturday, June 6th, 2026

View details for race Navy Federal Credit Union 5K- Winchester

Flip Flop 5K & Fun Run

Ashburn, VA

Saturday, June 6th, 2026

1 Mile

View details for race Flip Flop 5K & Fun Run

Barrel Oak Wine Run 5k

Delaplane, VA

Sunday, June 7th, 2026

View details for race Barrel Oak Wine Run 5k

Fauquier Education Farm 5K and Fun Run

Warrenton, VA

Saturday, June 13th, 2026

1 Mile

View details for race Fauquier Education Farm 5K and Fun Run

=PR= Races: Run with Dad 5K

Reston, VA

Sunday, June 21st, 2026

1 Mile

View details for race =PR= Races: Run with Dad 5K

Red White 'n Brew 5k

Ashburn, VA

Saturday, June 27th, 2026

1 Mile

View details for race Red White 'n Brew 5k

=PR= Races: Firecracker 5K for the Troops prese...

Reston, VA

Saturday, July 4th, 2026

View details for race =PR= Races: Firecracker 5K for the Troops presented by Leidos

FSRC Independence 5000

Frederick, MD

Saturday, July 4th, 2026

Trail

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Culpeper July 4th Freedom 5k

Culpeper, VA

Saturday, July 4th, 2026

View details for race Culpeper July 4th Freedom 5k

Fourth of July 5K Fun Run

Great Falls, VA

Saturday, July 4th, 2026

Trail

View details for race Fourth of July 5K Fun Run

Greg Shank Memorial 5K Run/Walk

Williamsport, MD

Saturday, July 4th, 2026

View details for race Greg Shank Memorial 5K Run/Walk

IMDC Freedom Firecracker 5K and Sparkler 1-Mile

Manassas, VA

Saturday, July 4th, 2026

1 Mile

View details for race IMDC Freedom Firecracker 5K and Sparkler 1-Mile

Glow All Out 5K Glow Run

Winchester, VA

Friday, July 17th, 2026

View details for race Glow All Out 5K Glow Run

Blue Crab Bolt Trail Run - Schaeffer Farms

Germantown, MD

Saturday, July 25th, 2026

Trail

Fast

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

SPEAR TRAIL SERIES

Stephens City, VA

Saturday, July 25th, 2026

Trail

View details for race SPEAR TRAIL SERIES

=PR= Races: Birthday Bash 5K

Ashburn, VA

Sunday, July 26th, 2026

View details for race =PR= Races: Birthday Bash 5K

Frederick Women's Distance Festival

Frederick, MD

Saturday, August 1st, 2026

View details for race Frederick Women's Distance Festival

Jack Roberts Memorial 5K

Hagerstown, MD

Sunday, August 9th, 2026

View details for race Jack Roberts Memorial 5K

Krumpe's Donut Alley Rally 5K

Hagerstown, MD

Friday, August 14th, 2026

View details for race Krumpe's Donut Alley Rally 5K

Chrysalis Vineyards Wine Run 5k

Middleburg, VA

Saturday, August 22nd, 2026

View details for race Chrysalis Vineyards Wine Run 5k

Explore more in Winchester, VA

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

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