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199 Sleepy Hollow Il Races All Cities

National Chocolate Day: Run for Chocolates DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-245684-1736915534.5077-0.bNHZPo.png

National Chocolate Day: Run for Chocolates DENVER/AURORA

Centennial, CO

Sat - Sep 13, 2025

Running > 5k, 10k, Half Marathon, 1 mile

All Hollowed Out 5K - Carlisle, PA - ultra-300px.bMjMog.png

All Hollowed Out 5K

Carlisle, PA

Sat - Sep 13, 2025

Running > Obstacle Race, 5k

Divas Chicago Half Marathon and 5k - Chicago, IL - genericImage-websiteLogo-251423-1743886119.5014-0.bN8zCN.png

Divas Chicago Half Marathon and 5k

Chicago, IL

Sat - Sep 13, 2025

Running > Half Marathon, 5k

Better Than Yesterday 5K - Oswego, IL - genericImage-websiteLogo-249786-1749133065.1412-0.bOqACj.png

Better Than Yesterday 5K

Oswego, IL

Sun - Sep 14, 2025

Run the River for Respect 5K - Ottawa, IL - ultra-300px.bMjMog.png

Run the River for Respect 5K

Ottawa, IL

Sun - Sep 14, 2025

Race to Recycle - South Beloit, IL - genericImage-websiteLogo-248763-1740421054.5157-0.bNVlE-.png

Race to Recycle

South Beloit, IL

Sat - Sep 20, 2025

Running > 5k, 1 mile, Walking

The Long Run - Chicago, IL - running-17.png

The Long Run

Chicago, IL

Sat - Sep 20, 2025

11th Annual Hustle Up the Hill Event - Warrenville, IL - d003feec-5818-448b-b907-514409d5d116.png

11th Annual Hustle Up the Hill Event

Warrenville, IL

Sat - Sep 20, 2025

2025 Amish Country Bicycle Tour - Arthur, IL - 213848ab-0147-4a62-ada9-4e3025d02306.jpg

2025 Amish Country Bicycle Tour

Arthur, IL

Sat - Sep 20, 2025

Limestone Rocks! 8-Hour or 4-Hour Race - Kankakee, IL - genericImage-websiteLogo-250828-1742845022.9877-0.bN4BrE.png

Limestone Rocks! 8-Hour or 4-Hour Race

Kankakee, IL

Sat - Sep 20, 2025

Our Fallen Hero 5K In Memory Of PFC Aaron Toppen - Mokena, IL - genericImage-websiteLogo-256087-1749568021.0032-0.bOseOv.png

Our Fallen Hero 5K In Memory Of PFC Aaron Toppen

Mokena, IL

Sat - Sep 20, 2025

Albion Artisan Brick Run - Albion, IL - genericImage-websiteLogo-256922-1750730689.1404-0.bOwGFb.png

Albion Artisan Brick Run

Albion, IL

Sat - Sep 20, 2025

Carlyle Lake Triathlon - Carlyle Township, IL - 2762511_400.jpg

Carlyle Lake Triathlon

Carlyle Township, IL

Sun - Sep 21, 2025 @ 7:00 AM

Triathlon > Duathlon, Olympic

North Shore Century 2025 - Wilmette, IL - 1e27bca6-a2d3-4bd2-962a-6a245593ed33.png

North Shore Century 2025

Wilmette, IL

Sun - Sep 21, 2025

Belleville Main Street Marathon

Belleville, IL

Sat - Sep 27, 2025 @ 7:00 AM

Running > Marathon, Half Marathon

Belleville Main Street Marathon & Half Marathon - Belleville, IL - genericImage-websiteLogo-244584-1735515389.4204-0.bNCDZ9.jpg

Belleville Main Street Marathon & Half Marathon

Belleville, IL

Sat - Sep 27, 2025

Running > Marathon, Half Marathon

Race to Cure Sarcoma Chicago - Chicago, IL - genericImage-websiteLogo-221623-1739994422.8573-0.bNTJu2.png

Race to Cure Sarcoma Chicago

Chicago, IL

Sat - Sep 27, 2025

Running > 5k, 1k

Chicago 10k, 5k, Half 13.1 - Chicago, IL - running-2.png

Chicago 10k, 5k, Half 13.1

Chicago, IL

Sep 27, 2025 - Sep 28, 2025

National Singles Day: Singles & Friends Running Club CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-245801-1737011662.0787-0.bNIlho.png

National Singles Day: Singles & Friends Running Club CHICAGO/EVANSTON

Chicago, IL

Sat - Sep 27, 2025

Running > 1 mile, 10k, 5k, Half Marathon

National Coffee Day: Run for Coffee CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-245687-1736919464.0351-0.bNH0MO.png

National Coffee Day: Run for Coffee CHICAGO/EVANSTON

Chicago, IL

Sat - Sep 27, 2025

Running > 5k, 10k, Half Marathon, 1 mile

Bloomingdale Trail 5K - Chicago, IL - running-7.png

Bloomingdale Trail 5K

Chicago, IL

Sat - Sep 27, 2025

Chick-Fil-A 5K - Naperville, IL - 5k_2025_Approved_Logo__2_.png

Chick-Fil-A 5K

Naperville, IL

Sat - Sep 27, 2025 @ 9:00 AM

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National Singles Day: Singles & Friends Running DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-245801-1737011662.0787-0.bNIlho.png

National Singles Day: Singles & Friends Running DENVER/AURORA

Centennial, CO

Sat - Sep 27, 2025

Running > 5k, 10k, Half Marathon, 1 mile

Friends of the Poor Walk SVDP Holy Trinity Westmont - Westmont, IL - genericImage-websiteLogo-255147-1748457768.352-0.bOn1KO.png

Friends of the Poor Walk SVDP Holy Trinity Westmont

Westmont, IL

Sat - Sep 27, 2025

Running > Walking

5K For Foster Youth - Chicago, IL - genericImage-websiteLogo-253066-1745523822.2875-0.bOcPrU.png

5K For Foster Youth

Chicago, IL

Sat - Sep 27, 2025

Miles for Marshall 5K Trail Run for Childhood Cancer - Greenville, IL - genericImage-websiteLogo-254087-1746792925.2899-0.bOhFhD.png

Miles for Marshall 5K Trail Run for Childhood Cancer

Greenville, IL

Sat - Sep 27, 2025

St. Jude Walk-Chicago - Brookfield, IL - genericImage-websiteLogo-257396-1751383564.8234-0.bOy_4m.jpg

St. Jude Walk-Chicago

Brookfield, IL

Sat - Sep 27, 2025

Walk4Animals & 5K Run

Batavia, IL

Sun - Sep 28, 2025 @ 08:00

Prairie Pedal 2025 - Decatur, IL - 16fa396a-f2e0-4b99-9b15-27262b649c88.jpg

Prairie Pedal 2025

Decatur, IL

Sep 28, 2025 - Sep 29, 2025

Gift of Hope Community Foundation 5K Run, Walk & Roll - Glen Ellyn, IL - genericImage-websiteLogo-249125-1740755704.1606-0.bNWDl4.png

Gift of Hope Community Foundation 5K Run, Walk & Roll

Glen Ellyn, IL

Sun - Sep 28, 2025

Running > 5k, 1 mile