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52 Sleepy Hollow Il Races All Cities

Run the River for Respect 5K - Ottawa, IL - genericImage-websiteLogo-255460-1765386799.8911-0.bPoAOV.png

Run the River for Respect 5K

Ottawa, IL

Sun - Sep 27, 2026

Run for Honor - Springfield, IL - running-10.png

Run for Honor

Springfield, IL

Sun - Sep 27, 2026

Golden Harvest Half Marathon & 5k/10k - Greater Chicago - Greater Chicago, IL - genericImage-websiteLogo-266273-1761328678.0091-0.bO-74M.png

Golden Harvest Half Marathon & 5k/10k - Greater Chicago

Greater Chicago, IL

Sun - Sep 27, 2026

Running > 5k, Half Marathon, 1 mile

Will to Ben powered by Bike Wisconsin - Port Byron, IL - picture12007.jpg

Will to Ben powered by Bike Wisconsin

Port Byron, IL

Oct 3, 2026 - Oct 9, 2026 (10:00 AM)

Cycling > Century, Half Century, Metric Century, Other Cycling

Dana Peak Trail Run - Harker Heights, TX - Dana-Peak-Web.png

Dana Peak Trail Run

Harker Heights, TX

Oct 3, 2026 - Oct 4, 2026 (6:00 AM)

Running > 10 Mile, Trail, Ultra, 10k

VIEW DISCOUNT

Haunted Wine Run 5k at Busse Woods - Elk Grove Village, IL - haunted-wine-run-5k-at-busse-woods-logo_U3IlnVQ.png

Haunted Wine Run 5k at Busse Woods

Elk Grove Village, IL

Sat - Oct 03, 2026 @ 15:00

2026 Bucktown 5K and Kids' Run - Chicago, IL - 3338444.jpg

2026 Bucktown 5K and Kids' Run

Chicago, IL

Sun - Oct 04, 2026 @ 8:30 AM

Operation Jake - Herrin, IL - running-8.png

Operation Jake

Herrin, IL

Sat - Oct 10, 2026

Cookie Run 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-270827-1768499663.1178-0.bPAsNp.png

Cookie Run 5K/10K/13.1 DENVER/AURORA

Centennial, CO

Sat - Oct 10, 2026

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

Cookie Run 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-270827-1768499663.1178-0.bPAsNp.png

Cookie Run 5K/10K/13.1 CHICAGO/EVANSTON

Chicago, IL

Sat - Oct 10, 2026

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

Sauk Valley Apple Cider Run - Rock Falls, IL - genericImage-websiteLogo-272584-1768941470.8518-0.bPB-EE.jpg

Sauk Valley Apple Cider Run

Rock Falls, IL

Sat - Oct 10, 2026

Running > Half Marathon, 5k

Bank of America Chicago Marathon 2026 - Chicago, IL - 400.jpg

Bank of America Chicago Marathon 2026

Chicago, IL

Sun - Oct 11, 2026 @ 7:30 AM

Running > Marathon

6 Week Fall Series- Palos - Palos Heights, IL - ce578a07-62ab-49aa-8318-97e8a3625978.jpg

6 Week Fall Series- Palos

Palos Heights, IL

Oct 15, 2026 - Nov 19, 2026

Red Sneakers Peoria 5K & Teal Pumpkin Festival - Peoria Heights, IL - red-sneakers-peoria-5k-teal-pumpkin-festival-logo_DYRqwac.png

Red Sneakers Peoria 5K & Teal Pumpkin Festival

Peoria Heights, IL

Sat - Oct 17, 2026 @ 09:00

Triathlon > Duathlon

Haunted Highlander Assault Trail Run - Pingree Grove, IL - genericImage-websiteLogo-264099-1758728650.0548-0.bO1bhk.png

Haunted Highlander Assault Trail Run

Pingree Grove, IL

Fri - Oct 23, 2026

Running > Obstacle Race, 5k

2026 Will Run for Beer Chicago 5K - Chicago, IL - 3338482_200.jpg

2026 Will Run for Beer Chicago 5K

Chicago, IL

Sat - Oct 24, 2026 @ 3:00 PM

Marshall Rotary Jack-O-Jog - Marshall, IL - genericImage-websiteLogo-265245-1759867649.0211-0.bO5xmb.png

Marshall Rotary Jack-O-Jog

Marshall, IL

Sat - Oct 24, 2026

Running > 1 mile, 5k

2026 SKECHERS Wicked Wine Run Chicago - Wheaton, IL - d0f94a7b-45fe-4d73-afda-e419613210d5.png

2026 SKECHERS Wicked Wine Run Chicago

Wheaton, IL

Oct 24, 2026 - Oct 25, 2026

Running > 5k, 1k

The Copper Penny Spirits Halloween Eve 5k - Vandalia, IL - genericImage-websiteLogo-276329-1772325543.7891-0.bPO4QN.png

The Copper Penny Spirits Halloween Eve 5k

Vandalia, IL

Fri - Oct 30, 2026

PB&J Fuel Run 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-271248-1768499966.5873-0.bPAsR-.png

PB&J Fuel Run 5K/10K/13.1 DENVER/AURORA

Centennial, CO

Sat - Oct 31, 2026

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

PB&J Fuel Run 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-271248-1768499966.5873-0.bPAsR-.png

PB&J Fuel Run 5K/10K/13.1 CHICAGO/EVANSTON

Chicago, IL

Sat - Oct 31, 2026

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

2026 UNO Carrera De Las Muertos/Race of the Dead event - Chicago, IL - 1158e845-0513-46a1-a2f1-879078d73a75.png

2026 UNO Carrera De Las Muertos/Race of the Dead event

Chicago, IL

Oct 31, 2026 - Nov 1, 2026

Howling Habitat 5K/Fun Run - O'Fallon, IL - running-11.png

Howling Habitat 5K/Fun Run

O'Fallon, IL

Sat - Oct 31, 2026

2026 Eerie Erie - Erie, CO - e73280cd-15c8-46b1-936f-3b2be94a8718.png

2026 Eerie Erie

Erie, CO

Sat - Oct 31, 2026

Running > 10k, 5k

2026 SKECHERS Hot Chocolate Run Chicago - Chicago, IL - 3338487_200.jpg

2026 SKECHERS Hot Chocolate Run Chicago

Chicago, IL

Sun - Nov 01, 2026 @ 7:30 AM

Pocantico Hills Races - Tarrytown, NY - genericImage-websiteLogo-269838-1765832899.2657-0.bPqhJd.png

Pocantico Hills Races

Tarrytown, NY

Sat - Nov 07, 2026

Running > Marathon, Half Marathon, Walking

City of the Sun 5K Trail Run 2026 - Collinsville, IL - running-14.png

City of the Sun 5K Trail Run 2026

Collinsville, IL

Sun - Nov 08, 2026

Run for Mental Health 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-270815-1768499680.5521-0.bPAsNG.png

Run for Mental Health 5K/10K/13.1 DENVER/AURORA

Centennial, CO

Sat - Nov 14, 2026

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

Run for Mental Health 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-270815-1768499680.5521-0.bPAsNG.png

Run for Mental Health 5K/10K/13.1 CHICAGO/EVANSTON

Chicago, IL

Sat - Nov 14, 2026

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

Run for Mental Health 5K/10K/13.1 MEMPHIS - Memphis, TN - genericImage-websiteLogo-270815-1768499680.5521-0.bPAsNG.png

Run for Mental Health 5K/10K/13.1 MEMPHIS

Memphis, TN

Sat - Nov 14, 2026

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