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84 Sleepy Hollow Il Races All Cities

29th Annual Naperville Rotary Ride - Naperville, IL - 7c14fdde-b860-449b-b7a2-fab5870b6704.png

29th Annual Naperville Rotary Ride

Naperville, IL

Sun - Aug 09, 2026

Highlander Assault Obstacle Race - Pingree Grove, IL - genericImage-websiteLogo-262924-1758395416.0477-0.bOZVWy.png

Highlander Assault Obstacle Race

Pingree Grove, IL

Sat - Aug 15, 2026

Running > Obstacle Race, 5k, 10k

Lena Brew Run 5k - Lena, IL - lena-brew-run-5k-logo_PJrWrCU.png

Lena Brew Run 5k

Lena, IL

Sat - Aug 15, 2026 @ 09:00

Run for PB& J 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-271773-1768497575.4432-0.bPAsgN.png

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

Centennial, CO

Sat - Aug 15, 2026

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

2026 Wyalusing North Branch Triathlon - Wyalusing, PA - a7eb28ad-d928-4913-99a7-f08b316a62a1.jpg

2026 Wyalusing North Branch Triathlon

Wyalusing, PA

Sat - Aug 15, 2026

Flight to the Finish - Zion, IL - ultra-300px.bMjMog.png

Flight to the Finish

Zion, IL

Sat - Aug 15, 2026

Run for PB& J 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-271767-1768497528.5278-0.bPAsf4.png

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

Chicago, IL

Sat - Aug 15, 2026

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

Bubble Run | St Louis 2026 - Sauget, IL - 4c30b0b2-d7c3-4cd9-89cd-ab345ccff974.png

Bubble Run | St Louis 2026

Sauget, IL

Aug 15, 2026 - Aug 16, 2026

2026 Chicago Triathlon - Chicago, IL - dcf688a5-9dad-466d-9f20-f82276a7fe56.png

2026 Chicago Triathlon

Chicago, IL

Aug 22, 2026 - Aug 25, 2026

Triathlon > Super Sprint, Sprint, Olympic

Let's Play Sports Clinic - Chicago, IL - running-9.png

Let's Play Sports Clinic

Chicago, IL

Sat - Aug 22, 2026

Sloth Run 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-271274-1768498380.3273-0.bPAstm.png

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

Centennial, CO

Sat - Aug 29, 2026

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

Sloth Run 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-271268-1768498218.546-0.bPAsqQ.png

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

Chicago, IL

Sat - Aug 29, 2026

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

Tails on the Trail 5K & 1-Mile Wag & Walk - Matteson, IL - genericImage-websiteLogo-274194-1770670182.02-0.bPIKHM.png

Tails on the Trail 5K & 1-Mile Wag & Walk

Matteson, IL

Sat - Aug 29, 2026

Running > 1 mile, 5k

Rise & Run for Recovery - Lake Villa, IL - genericImage-websiteLogo-275433-1773168236.3202-0.bPSgzS.png

Rise & Run for Recovery

Lake Villa, IL

Sun - Aug 30, 2026

Sidewinder - Coraopolis, PA - ultra-300px.bMjMog.png

Sidewinder

Coraopolis, PA

Sat - Sep 05, 2026

Running > Obstacle Race, Half Marathon

Sweetcorn 5K Classic 2026 - Hoopeston, IL - a31c65ff-7f1c-45c4-bd28-a21fcaf62eed.png

Sweetcorn 5K Classic 2026

Hoopeston, IL

Sat - Sep 05, 2026

Odyssey Trail Running Rampage - Millboro, VA - genericImage-websiteLogo-235882-1724084468.0419-0.bMW3d0.png

Odyssey Trail Running Rampage

Millboro, VA

Sat - Sep 12, 2026

Running > Obstacle Race

National Chocolate Day: Run for Chocolates 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-271314-1768498886.8218-0.bPAsBg.png

National Chocolate Day: Run for Chocolates 5K/10K/13.1 DENVER/AURORA

Centennial, CO

Sat - Sep 12, 2026

National Chocolate Day: Run for Chocolates 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-271303-1768498846.8793-0.bPAsAE.png

National Chocolate Day: Run for Chocolates 5K/10K/13.1 CHICAGO/EVANSTON

Chicago, IL

Sat - Sep 12, 2026

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

Tunnel to Towers Climb - Chicago, IL

Chicago, IL

Sat - Sep 12, 2026

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 13, 2026

Running > 5k, 1 mile

Runway To a Cure - Ottawa, IL - genericImage-websiteLogo-274220-1770691458.0101-0.bPIPUc.png

Runway To a Cure

Ottawa, IL

Sat - Sep 19, 2026

Running > 5k, 1k

Limestone Rocks! 8-Hour or 4-Hour Race - Kankakee, IL - genericImage-websiteLogo-250828-1772150205.3508-0.bPOn29.jpg

Limestone Rocks! 8-Hour or 4-Hour Race

Kankakee, IL

Sat - Sep 19, 2026

Divas Chicago Half Marathon & 5k - Chicago, IL - c23e093b-58a8-4284-a1ff-6c56fd04a3c9.png

Divas Chicago Half Marathon & 5k

Chicago, IL

Sep 19, 2026 - Sep 20, 2026

Running > 5k, Half Marathon

Russell's Ride 2026 for Cinnamon Center Christian School - Rogersville, TN - 077e3dfa-e180-4ccb-bc43-71257212461f.jpeg

Russell's Ride 2026 for Cinnamon Center Christian School

Rogersville, TN

Sat - Sep 19, 2026

Carlyle Lake Triathlon - Carlyle Township, IL - 3370672400.jpg

Carlyle Lake Triathlon

Carlyle Township, IL

Sun - Sep 20, 2026 @ 7:00 AM

5K Fun Run/Walk - Glenview, IL - genericImage-websiteLogo-121891-1750283480.4779-0.bOuZty.jpg

5K Fun Run/Walk

Glenview, IL

Sun - Sep 20, 2026

Headless Horseman Hussle - Sleepy Hollow, IL - genericImage-websiteLogo-277212-1773149638.4371-0.bPSb3g.png

Headless Horseman Hussle

Sleepy Hollow, IL

Sun - Sep 20, 2026

North Shore Century 2026 - Wilmette, IL - 1e27bca6-a2d3-4bd2-962a-6a245593ed33.png

North Shore Century 2026

Wilmette, IL

Sun - Sep 20, 2026

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 26, 2026