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128 Sleepy Hollow Il Races All Cities

ENDO 5K - Chicago, IL - running-5.png

ENDO 5K

Chicago, IL

Tue - Jun 16, 2026

Sloth Run 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-263455-1768465513.3455-0.bPAkrP.png

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

Chicago, IL

Sat - Jun 20, 2026

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

DC Estate Wine Run 5k - South Beloit, IL - dc-estate-wine-run-5k-logo_a2QZ5cg.png

DC Estate Wine Run 5k

South Beloit, IL

Sat - Jun 20, 2026 @ 09:00

Sloth Run 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-263457-1768465566.9276-0.bPAksE.png

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

Centennial, CO

Sat - Jun 20, 2026

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

HIS Kids Cancer Support 5K - Granite City, IL - genericImage-websiteLogo-274485-1770942874.5867-0.bPJNgA.png

HIS Kids Cancer Support 5K

Granite City, IL

Sat - Jun 20, 2026

Run for Their Lives 5K - Mokena, IL - genericImage-websiteLogo-275559-1771606321.927-0.bPMjeX.jpg

Run for Their Lives 5K

Mokena, IL

Sat - Jun 20, 2026

Sesser Homecoming 5k - Sesser, IL - walk-shoe-300px.bMjMog.png

Sesser Homecoming 5k

Sesser, IL

Sat - Jun 20, 2026

Running > 5k, Walking

Jasper Mountain Trail Fest 2026 - Dayton, WA - genericImage-websiteLogo-222762-1731355837.5999-0.bNmMs9.png

Jasper Mountain Trail Fest 2026

Dayton, WA

Sat - Jun 20, 2026

Running > Obstacle Race, Half Marathon, Marathon

Shoebox 5K and 1 Mile Run/Walk - Davis, IL - genericImage-websiteLogo-277517-1773259199.1499-0.bPSCM_.jpg

Shoebox 5K and 1 Mile Run/Walk

Davis, IL

Sat - Jun 20, 2026

Running > 5k, 1 mile

Ride Across Illinois (RAIL) North powered by Bicycle Illinois - Moline, IL - picture04280.jpg

Ride Across Illinois (RAIL) North powered by Bicycle Illinois

Moline, IL

Sun - Jun 21, 2026 @ 5:30 AM

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

Pura Vida 5K Fun Run/Walk - Wood Dale, IL - genericImage-websiteLogo-276488-1772641012.1471-0.bPQfR0.png

Pura Vida 5K Fun Run/Walk

Wood Dale, IL

Sun - Jun 21, 2026

POLONIADA 5K RUN & WALK 2026 - Elk Grove Village, IL - 0f223813-417d-47e8-86cd-a41c613b44da.jpg

POLONIADA 5K RUN & WALK 2026

Elk Grove Village, IL

Sun - Jun 21, 2026

Iowa Trail Run Series: Sleepy Hollow - Des Moines, IA - running-9.png

Iowa Trail Run Series: Sleepy Hollow

Des Moines, IA

Sat - Jun 27, 2026

"Run the Ridge LAKE FRONT" Mary E. Smith 17th Annual Brain Tumor Awareness 5K Event - Chicago, IL - genericImage-websiteLogo-246496-1737954272.2143-0.bNLXpG.png

"Run the Ridge LAKE FRONT" Mary E. Smith 17th Annual Brain Tumor Awareness 5K Event

Chicago, IL

Sat - Jun 27, 2026

The Universal Sole Summer Trail Challenge - Willow Springs, IL - genericImage-websiteLogo-275722-1771868177.1627-0.bPNjar.jpg

The Universal Sole Summer Trail Challenge

Willow Springs, IL

Sat - Jun 27, 2026

Running > Obstacle Race, 5k, 5 mile

Shamrock Race to the Cross 2026 - Effingham, IL - running-14.png

Shamrock Race to the Cross 2026

Effingham, IL

Jun 27, 2026 - Jun 28, 2026

Run for Chocolate 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-263490-1768494384.5677-0.bPAruW.png

Run for Chocolate 5K/10K/13.1 CHICAGO/EVANSTON

Chicago, IL

Sat - Jul 04, 2026

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

Reagan Run - Dixon, IL - genericImage-websiteLogo-268527-1765816079.4642-0.bPqdCp.png

Reagan Run

Dixon, IL

Sat - Jul 04, 2026

Run for Chocolate 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-263495-1768494418.3821-0.bPArvs.png

Run for Chocolate 5K/10K/13.1 DENVER/AURORA

Centennial, CO

Sat - Jul 04, 2026

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

Ring My Bell 2026 - Oreana, IL - genericImage-websiteLogo-277012-1773105140.6721-0.bPR2_0.jpg

Ring My Bell 2026

Oreana, IL

Sat - Jul 04, 2026

Elmhurst Running Club 4 on the 4th - Elmhurst, IL - genericImage-websiteLogo-276774-1773002676.6011-0.bPRD-0.jpg

Elmhurst Running Club 4 on the 4th

Elmhurst, IL

Sat - Jul 04, 2026

Running > 5k, 1k

4 Miles on the 4th - Canton, IL - genericImage-websiteLogo-273123-1772834403.0158-0.bPQ05J.png

4 Miles on the 4th

Canton, IL

Sat - Jul 04, 2026

Running > 5k, 1 mile

Stars and Stripes - America's 250th Anniversary Challenge - Lake Zurich, IL - genericImage-websiteLogo-278261-1774533395.5793-0.bPXtSt.png

Stars and Stripes - America's 250th Anniversary Challenge

Lake Zurich, IL

Mar 26, 2026 - Jul 12, 2026

Running > 5k, 10k, Half Marathon

Treat Trot Greater Chicago

Greater Chicago, IL

Sun - Jul 05, 2026

Running > 5k, 10k

Central Illinois Summer Trail Series #2 - Metamora, IL - genericImage-websiteLogo-276067-1772550915.6765-0.bPPVSd.png

Central Illinois Summer Trail Series #2

Metamora, IL

Fri - Jul 10, 2026

Running > Obstacle Race, 5 mile

Savage Race Chicago 2026 - Spring Grove, IL - genericImage-websiteLogo-239250-1728494920.0989-0.bNbR1i.png

Savage Race Chicago 2026

Spring Grove, IL

Sat - Jul 11, 2026

Running > 5 mile, 5k, 1 mile, Obstacle Race

Biking with Beanzie - Dekalb, IL - d052127e-b7e0-4d2c-a0bc-30cfca22bc0a.jpg

Biking with Beanzie

Dekalb, IL

Sun - Jul 12, 2026

Polka Run 5K - Chicago, IL - genericImage-websiteLogo-274174-1770662617.3751-0.bPIIRz.jpg

Polka Run 5K

Chicago, IL

Sun - Jul 12, 2026

2026 Lake Zurich Triathlon - Lake Zurich, IL - 65e8a18a-128c-4c06-8883-4f16557bdd9f.png

2026 Lake Zurich Triathlon

Lake Zurich, IL

Jul 12, 2026 - Jul 13, 2026

Triathlon > Olympic, Sprint

2026 Heartland Series - Day 4 (IL) - Fulton, IL - 0fe8efc4-838a-4820-8725-eb975da710d5.png

2026 Heartland Series - Day 4 (IL)

Fulton, IL

Jul 14, 2026 - Jul 15, 2026

Running > Marathon