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108 Sleepy Hollow Il Races All Cities

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 > 5 mile, Obstacle Race

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

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

Mud Mountain XXX 5K Classic and Mile Fun Run - Edwardsville, IL - e2b214e2-084c-421b-928a-1c0b5ea459f7.png

Mud Mountain XXX 5K Classic and Mile Fun Run

Edwardsville, 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

Santa's Run - Middlefield, OH - running-14.png

Santa's Run

Middlefield, OH

Sat - Aug 01, 2026

Heatwave Half Marathon - Greater Chicago - Elk Grove Village, IL - genericImage-websiteLogo-263263-1757961856.1258-0.bOYf6a.png

Heatwave Half Marathon - Greater Chicago

Elk Grove Village, IL

Sun - Aug 02, 2026

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

Dawson Lake Dash - Le Roy, IL - genericImage-websiteLogo-274363-1770835726.5202-0.bPJm8o.png

Dawson Lake Dash

Le Roy, IL

Sun - Aug 02, 2026

Running > 1 mile

2026 Naperville Sprint Triathlon - Naperville, IL - 576fcfa2-1e3d-4139-8c28-d087ccc15e0f.png

2026 Naperville Sprint Triathlon

Naperville, IL

Aug 2, 2026 - Aug 3, 2026

Triathlon > Super Sprint, Sprint

SSW Running Club Club Challenge 5k - Tinley Park, IL - ssw-running-club-club-challenge-5k-logo_8L4HxvI.jpg

SSW Running Club Club Challenge 5k

Tinley Park, IL

Wed - Aug 05, 2026 @ 19:00

Central Illinois Summer Trail Series #3 - Washington, IL - genericImage-websiteLogo-276070-1772559044.2356-0.bPPXRe.png

Central Illinois Summer Trail Series #3

Washington, IL

Fri - Aug 07, 2026

Running > Obstacle Race, 5 mile

High Point Sprint Triathlon & Youth Triathlon - High Point, NC - 7aadbe93-b495-4701-9ef1-a708ea5e0cf6.jpg

High Point Sprint Triathlon & Youth Triathlon

High Point, NC

Sat - Aug 08, 2026 @ 7:45 AM

Triathlon > Sprint, Super Sprint

Back-to-School Family Fun 5K - Wheeling, IL - genericImage-websiteLogo-257727-1751913476.4751-0.bOBbqe.jpg

Back-to-School Family Fun 5K

Wheeling, IL

Sat - Aug 08, 2026

RUN FOR C'VILLE - Carpentersville, IL - genericImage-websiteLogo-276299-1773193757.9797-0.bPSmOD.png

RUN FOR C'VILLE

Carpentersville, IL

Sat - Aug 08, 2026

Ben's Memorial Mile & Community Festival - Downers Grove, IL - genericImage-websiteLogo-235329-1723224857.4202-0.bMTLmz.jpg

Ben's Memorial Mile & Community Festival

Downers Grove, IL

Sat - Aug 08, 2026

Running > 1 mile