Upcoming Races Near Shepherdstown, WV in May, 2026

Name: 39th Annual Loudoun Street Mile
Start: 2026-05-25
End: 2026-05-25
Location: Winchester

ChadTough Defeat DIPG Superhero Sprint & 6K

Bethesda, MD

Friday, May 1st, 2026

Featured

View details for race ChadTough Defeat DIPG Superhero Sprint & 6K

Want to feature your race?

Get your race seen first by thousands of runners

Learn More

Learn how to feature your race

Apple Blossom Valley Health 10K and Shenandoah ...

Winchester, VA

Friday, May 1st, 2026

1 Mile

10K

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

Luau 5K, 10K, & 13.1M at Biglerville, PA (18)

Biglerville, PA

Saturday, May 2nd, 2026

10K

Half

View details for race Luau 5K, 10K, & 13.1M at Biglerville, PA (18)

Cougar Literacy Run

Manassas Park, VA

Saturday, May 2nd, 2026

View details for race Cougar Literacy Run

MCRRC Kids on the Run

Gaithersburg, MD

Saturday, May 2nd, 2026

1 Mile

View details for race MCRRC Kids on the Run

Wood Acres JogFest

Bethesda, MD

Saturday, May 2nd, 2026

1 Mile

View details for race Wood Acres JogFest

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

View details for race Frederick Running Festival

Bethesda Elementary School Fun Run

Bethesda, MD

Saturday, May 2nd, 2026

1 Mile

View details for race Bethesda Elementary School Fun Run

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

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

Feed Fairfax 5K

Fairfax, VA

Saturday, May 2nd, 2026

1 Mile

View details for race Feed Fairfax 5K

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

Spencerville Adventist Academy Cross Country 5K...

Spencerville, MD

Sunday, May 3rd, 2026

1 Mile

Fast

View details for race Spencerville Adventist Academy Cross Country 5K, 1 Mile Race, and Kids Fun Run

MCRRC First Time Marathon (FTM) Program

Rockville, MD

Sunday, May 3rd, 2026

Marathon

View details for race MCRRC First Time Marathon (FTM) Program

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

Raccoon Run

Fairfax, VA

Saturday, May 9th, 2026

1 Mile

View details for race Raccoon Run

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

Inspire Life 5K

Gaithersburg, MD

Saturday, May 9th, 2026

View details for race Inspire Life 5K

Move for Mental Health

Warrenton, VA

Saturday, May 9th, 2026

View details for race Move for Mental Health

Deer Dash 5K and Fun Run

New Market, MD

Saturday, May 9th, 2026

1 Mile

View details for race Deer Dash 5K and Fun Run

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

Medal Madness 5K & 10K at Westminster, MD (19)

Westminster, MD

Saturday, May 9th, 2026

10K

View details for race Medal Madness 5K & 10K at Westminster, MD (19)

Ruck & Rosé 5K

Westminster, MD

Saturday, May 9th, 2026

View details for race Ruck & Rosé 5K

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

2nd Annual Eldersurg Elementary School PTA Colo...

Eldersburg, MD

Saturday, May 9th, 2026

1 Mile

View details for race 2nd Annual Eldersurg Elementary School PTA Color Run

EveryMile for EveryMind 5K and 1K Fun Run/Walk

Rockville, MD

Sunday, May 10th, 2026

View details for race EveryMile for EveryMind 5K and 1K Fun Run/Walk

=PR= Races: Mother's Day 4 Miler & 1 Miler bene...

Reston, VA

Sunday, May 10th, 2026

1 Mile

View details for race =PR= Races: Mother's Day 4 Miler & 1 Miler benefiting Devotion to Children

MCRRC Spring 10K Program

Rockville, MD

Wednesday, May 13th, 2026

10K

View details for race MCRRC Spring 10K Program

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

Woodson High School Eddie Zhou Charity 5K Run/Walk

Fairfax, VA

Saturday, May 16th, 2026

View details for race Woodson High School Eddie Zhou Charity 5K Run/Walk

Front Royal Kiwanis 5K

Front Royal, VA

Saturday, May 16th, 2026

View details for race Front Royal Kiwanis 5K

Race to Share the Gospel Around the World

Chambersburg, PA

Saturday, May 16th, 2026

Half

View details for race Race to Share the Gospel Around the World

Group run/ruck/walk with Shenandoah Valley Runn...

Winchester, VA

Saturday, May 16th, 2026

View details for race Group run/ruck/walk with Shenandoah Valley Runners and Girls on the Run of the Shenandoah Valley!

Harpers Ferry Half Marathon & 5K

Harpers Ferry, WV

Saturday, May 16th, 2026

Half

View details for race Harpers Ferry Half Marathon & 5K

MCRRC Run Aware 5K

Bethesda, MD

Sunday, May 17th, 2026

View details for race MCRRC Run Aware 5K

Spring RunFit Kidz Celebration Run

Fairfax, VA

Sunday, May 17th, 2026

View details for race Spring RunFit Kidz Celebration Run

Farm 5K Run/Walk at Wardensville Garden Market

Wardensville, WV

Saturday, May 23rd, 2026

View details for race Farm 5K Run/Walk at Wardensville Garden Market

Down the Stretch Track Fest

Fairfax, VA

Saturday, May 23rd, 2026

1 Mile

10K

View details for race Down the Stretch Track Fest

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

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

May 25th, Hamilton Day Mighty Miler

Hamilton, VA

Monday, May 25th, 2026

1 Mile

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

The 2026 10th Anniversary Highmark Wholecare Me...

Gettysburg, PA

Monday, May 25th, 2026

View details for race The 2026 10th Anniversary Highmark Wholecare Memorial Day Free 5K, presented by Healthy Adams County

MCRRC Memorial Day 4 Mile

Rockville, MD

Monday, May 25th, 2026

View details for race MCRRC Memorial Day 4 Mile

Panda 5K & 1K Fun Run

Frederick, MD

Monday, May 25th, 2026

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

39th Annual Loudoun Street Mile

Winchester, VA

Monday, May 25th, 2026

1 Mile

View details for race 39th Annual Loudoun Street Mile

Explore more in Shepherdstown, WV

Distances:

5K 10K Half Marathon Marathon

Months:

March April May

Tags:

Trail Boston Qualifiers Fast Courses

State:

All West Virginia races

Don't see your race? Add it!

Add Your Race (Free)