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193 Sleepy Hollow Il Races All Cities

5th Annual Boots and Brews 5K - Freeport, ME - genericImage-websiteLogo-253867-1746559177.913-0.bOgMdj.png

5th Annual Boots and Brews 5K

Freeport, ME

Sat - May 16, 2026

Spirits Run on the Rocks a Waukegan 5k

Waukegan, IL

Sat - May 16, 2026 @ 10:00

Running > Other Running

Family Service Association 5k - Elgin, IL - genericImage-websiteLogo-250787-1769113169.0654-0.bPCOzr.png

Family Service Association 5k

Elgin, IL

Sat - May 16, 2026

Bright Star Community Outreach 5K Run/Walk - Hope in Action - Chicago, IL - genericImage-websiteLogo-273421-1770141436.3173-0.bPGJB8.png

Bright Star Community Outreach 5K Run/Walk - Hope in Action

Chicago, IL

Sat - May 16, 2026

Run for Brain Health - Chadwick, IL - genericImage-websiteLogo-272545-1768930300.7969-0.bPB7V8.png

Run for Brain Health

Chadwick, IL

Sat - May 16, 2026

Running > 5k, 1 mile

Fast and Furriest 5k Year 12

Springfield, MO

Sat - May 16, 2026 @ 10:00

Wolf Lake 5k - Chicago, IL - genericImage-websiteLogo-250330-1742919508.2452-0.bN4TDu.jpg

Wolf Lake 5k

Chicago, IL

Sat - May 16, 2026

White Squirrel Roubaix - Olney, IL - genericImage-websiteLogo-275447-1771531656.3428-0.bPL22i.png

White Squirrel Roubaix

Olney, IL

Sat - May 16, 2026

Cary Hero Dash 5KM Walk/Run - Cary, IL - genericImage-websiteLogo-265810-1760648637.7027-0.bO8v29.png

Cary Hero Dash 5KM Walk/Run

Cary, IL

Sat - May 16, 2026

Hope Series - Sterling, IL - genericImage-websiteLogo-272592-1768944351.7554-0.bPB_lF.png

Hope Series

Sterling, IL

Sat - May 16, 2026

S2 Faction 5K - Bloomington - Bloomington, IL - genericImage-websiteLogo-272627-1769004101.2006-0.bPCnXf.png

S2 Faction 5K - Bloomington

Bloomington, IL

Sat - May 16, 2026

Lake Lou Yaeger Triathlon - Litchfield, IL - genericImage-websiteLogo-239263-1728504506.8743-0.bNbUk6.png

Lake Lou Yaeger Triathlon

Litchfield, IL

Sun - May 17, 2026

2026 Willard 5k Fun Run - River Forest, IL - genericImage-websiteLogo-276042-1771983255.3172-0.bPNLgx.png

2026 Willard 5k Fun Run

River Forest, IL

Sun - May 17, 2026

Run for Mental Health 5K/10K/13.1 DENVER/AURORA - Centennial, CO - genericImage-websiteLogo-263226-1768464052.5247-0.bPAj60.png

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

Centennial, CO

Sat - May 23, 2026

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

Run for Mental Health 5K/10K/13.1 CHICAGO/EVANSTON - Chicago, IL - genericImage-websiteLogo-263223-1768463929.4026-0.bPAj45.png

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

Chicago, IL

Sat - May 23, 2026

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

Rend Lake Run With Rotary - Benton, IL - genericImage-websiteLogo-250868-1742864982.0903-0.bN4Gjw.jpg

Rend Lake Run With Rotary

Benton, IL

Sat - May 23, 2026

Running > 10k, 5k

The LaSalle 9th Street Pub Spirits Dash - La Salle, IL - genericImage-websiteLogo-272900-1769236277.6913-0.bPDgC1.png

The LaSalle 9th Street Pub Spirits Dash

La Salle, IL

Sat - May 23, 2026

Onarga ALA Poppy 5K - Onarga, IL - genericImage-websiteLogo-222860-1772910428.0943-0.bPRhDC.png

Onarga ALA Poppy 5K

Onarga, IL

Sat - May 23, 2026

Cooper's Hawk Wine Run 5k

New Lenox, IL

Sun - May 24, 2026

Ruck It 2 - Yorkville, IL - genericImage-websiteLogo-276450-1772512723.083-0.bPPMxt.png

Ruck It 2

Yorkville, IL

Sun - May 24, 2026

Clayton's Tap Spirits Run - Morris, IL - genericImage-websiteLogo-275364-1771456847.561-0.bPLKLp.png

Clayton's Tap Spirits Run

Morris, IL

Sun - May 24, 2026

2026 Meatballs on the Run 5K - Benld, IL - genericImage-websiteLogo-276761-1772735647.7653-0.bPQCYF.png

2026 Meatballs on the Run 5K

Benld, IL

Sun - May 24, 2026

Marin Memorial 5 Mile - Novato, CA - genericImage-websiteLogo-276938-1773031996.1458-0.bPRLi8.png

Marin Memorial 5 Mile

Novato, CA

Mon - May 25, 2026

Running > 5 mile

Deuces Wild Endurance Festival Triathlons 2026 - Show Low, AZ - c480f1f1-4d05-4e86-bd79-c5713817f960.jpg

Deuces Wild Endurance Festival Triathlons 2026

Show Low, AZ

May 30, 2026 - May 31, 2026

Triathlon > Olympic, Sprint

Southern Illinois Tobacco Prevention Partnership 5K Run/ Walk - Carterville, IL - running-7.png

Southern Illinois Tobacco Prevention Partnership 5K Run/ Walk

Carterville, IL

Sat - May 30, 2026

South Fork Fly Fishing Tournament - Bentonville, VA - genericImage-websiteLogo-269023-1769201530.3012-0.bPC996.png

South Fork Fly Fishing Tournament

Bentonville, VA

Sat - May 30, 2026

Dan Gibbons Twilight Trot - Elmhurst, IL - genericImage-websiteLogo-246948-1740007178.3154-0.bNTMCk.png

Dan Gibbons Twilight Trot

Elmhurst, IL

Sat - May 30, 2026

2026 Night Nation Run - Chicago, IL - Chicago, IL - 400.jpg

2026 Night Nation Run - Chicago, IL

Chicago, IL

Sat - May 30, 2026 @ 8:30 PM

WARRIOR RUSH 5K - 10K - Half Marathon 13.1 (Chicagoland) - Wheaton, IL - genericImage-websiteLogo-276147-1772146995.0951-0.bPOneZ.jpg

WARRIOR RUSH 5K - 10K - Half Marathon 13.1 (Chicagoland)

Wheaton, IL

Sat - May 30, 2026

Running > Half Marathon, 10k, 5k

Brookfield Zoo Chicago Dino Dash - Brookfield, IL - running-13.png

Brookfield Zoo Chicago Dino Dash

Brookfield, IL

Sat - May 30, 2026