September Classic Races within 50 miles of Winchester, VA
City Location
1. Montgomery County Interfaith 5K
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Past DateSep 2, 2024Monday
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5K run | kids run
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Boyds, MD
45 miles point to pointMontgomery County, MD
2. Othello Park Labor Day 1K/5K
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Past DateSep 2, 2024Monday
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5K, 1K run
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Knoxville, MD
29 miles point to pointFrederick County, MD
3. Lock 2 Lock Marathon
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Sep 6, 2025Saturday
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26.2M, 13.1M, 10K run
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Williamsport, MD
35 miles point to pointWashington County, MD
4. The Inferno 5K & 10K
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Sep 6, 2025Saturday
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10K, 5K trail run
Virtual OptionMore Information
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Bluemont, VA
18 miles point to pointLoudoun County, VA
5. Pleasant Valley Aquathlon and 5K
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Past DateSep 7, 2024Saturday
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sprint aquathon | 5K run
Virtual OptionMore Information
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Chantilly, VA
45 miles point to pointFairfax County, VA
6. Race for the Cause 5K
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Past DateSep 7, 2024Saturday
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5K, 1M run
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Middletown, VA
12 miles point to pointFrederick County, VA
7. Victoria's Race Against Child Abuse
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Past DateSep 7, 2024Saturday
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5K run | kids run
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Inwood, WV
14 miles point to pointBerkeley County, WV
8. Run For Charity
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Past DateSep 8, 2024Sunday
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5K run
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Ashburn, VA
37 miles point to pointLoudoun County, VA
9. Shenandoah Half Marathon
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Sep 13, 2025Saturday
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13.1M run
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Luray, VA
38 miles point to pointPage County, VA
10. Sherando Park Endurance Athletic Run 8 Hour Challenge
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Sep 13, 2025Saturday
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8H trail run
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Stephens City, VA
7 miles point to pointFrederick County, VA
11. Frederick Market Street Mile
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Past DateSep 14, 2024Saturday
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1M run
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Frederick, MD
43 miles point to pointFrederick County, MD
12. Spring Valley View Hard Cider Challenge
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Sep 14, 2025Sunday
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13.1M, 10K, 5K trail run
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Delaplane, VA
22 miles point to pointFauquier County, VA
13. Wits for Wellness 5K
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Past DateSep 14, 2024Saturday
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5K run
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Middletown, VA
12 miles point to pointFrederick County, VA
14. Cacapon Resort State Park 5K
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Past DateSep 21, 2024Saturday
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5K run
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Berkeley Springs, WV
31 miles point to pointMorgan County, WV
15. Cinnamon Bun Fun Run
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Past DateSep 21, 2024Saturday
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5K run
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Smithsburg, MD
46 miles point to pointWashington County, MD
16. For God and Country
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Past DateSep 21, 2024Saturday
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2M run | 2M, 1M obstacle run
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Front Royal, VA
18 miles point to pointWarren County, VA
17. Halfway to St. Patrick's Day 5K!
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Past DateSep 21, 2024Saturday
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5K, 1M run
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Warrenton, VA
38 miles point to pointFauquier County, VA
18. Mental Health Heroes 5K
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Past DateSep 21, 2024Saturday
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5K run
Virtual OptionMore Information
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Haymarket, VA
38 miles point to pointPrince William County, VA
19. Oktoberfest 5K
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CancelledSep 21, 2024Saturday
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5K trail run | kids run
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Lovettsville, VA
29 miles point to pointLoudoun County, VA
20. Poolesville Day 5K
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Past DateSep 21, 2024Saturday
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5K run
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Poolesville, MD
40 miles point to pointMontgomery County, MD
For the love of all that Is good And moisture wicking...
Though we Try To be accurate And On top Of things... Race details can change When we aren't lookin. And once in a while we simply make a mistake.
ALWAYS visit the race's website for the most complete and accurate race information.
ALWAYS visit the race's website for the most complete and accurate race information.