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118 Sleepy Hollow Il Races All Cities

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 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

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

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

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

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

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

Treat Trot Greater Chicago

Greater Chicago, IL

Sun - Jul 05, 2026

Running > 10k, 5k

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

Christmas in July Half Marathon and 5K (Chicago area) - Elk Grove Village, IL - christmas-in-july-half-marathon-and-5k-chicago-area-logo_uGGSUYt.png

Christmas in July Half Marathon and 5K (Chicago area)

Elk Grove Village, IL

Sat - Jul 18, 2026 @ 07:00

RAGBRAI Transportation: Chicago to the Start of RAGBRAI powered by Bicycle Illinois - Chicago, IL - picture395.jpg

RAGBRAI Transportation: Chicago to the Start of RAGBRAI powered by Bicycle Illinois

Chicago, IL

Sat - Jul 18, 2026 @ 7:00 AM

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

Stan's Donut Race

Chicago, IL

Sat - Jul 18, 2026 @ 7:00 AM

Running > 10 Mile, 5k, Fun Run

Run for the Dogs 5k - Aurora - Aurora, IL - run-for-the-dogs-5k-aurora-logo_1o9dRbD.png

Run for the Dogs 5k - Aurora

Aurora, IL

Sat - Jul 18, 2026 @ 08:00

Stan's Donut 10K, 5K, and Kids Dash - Chicago, IL - 400.jpg

Stan's Donut 10K, 5K, and Kids Dash

Chicago, IL

Sat - Jul 18, 2026 @ 7:00 AM

The Opie's 116 Spirits Run - Roanoke, IL - genericImage-websiteLogo-275330-1771449795.8496-0.bPLI3d.png

The Opie's 116 Spirits Run

Roanoke, IL

Sat - Jul 18, 2026

Run for Coffee Lovers 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-262943-1768466703.4183-0.bPAkKp.png

Run for Coffee Lovers 5K/10K/13.1 DENVER/AURORA

Centennial, CO

Sat - Jul 25, 2026

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

Run for Coffee Lovers 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-262941-1768466659.14-0.bPAkJJ.png

Run for Coffee Lovers 5K/10K/13.1 CHICAGO/EVANSTON

Chicago, IL

Sat - Jul 25, 2026

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

Rhythm of the Heart 5k Race & Walk - Loves Park, IL - genericImage-websiteLogo-273631-1770052218.2805-0.bPGnP6.png

Rhythm of the Heart 5k Race & Walk

Loves Park, IL

Sat - Jul 25, 2026

11th Annual 5-O 5K Donut Run/Walk Presented by McLanahan Towing & Collision and TekLab Inc. - Collinsville, IL - 57b273c5-41bb-4a02-8cc4-58f69ebcf60c.png

11th Annual 5-O 5K Donut Run/Walk Presented by McLanahan Towing & Collision and TekLab Inc.

Collinsville, IL

Sat - Jul 25, 2026

Wauconda Triathlons 2026 - Wauconda, IL - triathlon-1.png

Wauconda Triathlons 2026

Wauconda, IL

Sun - Jul 26, 2026

Triathlon > Olympic, Sprint

AOTK Nourish the Nations 5k Color Run/Walk - Geneseo, IL - genericImage-websiteLogo-272361-1771451910.0198-0.bPLJyg.png

AOTK Nourish the Nations 5k Color Run/Walk

Geneseo, IL

Sat - Aug 01, 2026