October Classic Races within 50 miles of Pleasant Prairie, WI
Elkhorn, WI
Elkhorn Oktoberfest 5K
Oct 21, 2023
Mount Prospect, IL
Lemons of Love Pink Lemonade 5K
Oct 6, 2024
Palatine, IL
Halloween Hustle 5K and Kids Dash
Oct 26, 2024
Geneva, IL
Run, Walk & Roll
Oct 15, 2023
Racine, WI
Ted Miller Memorial 5K Run
Oct 1, 2023
Glenview, IL
NSSRA Run for All
Oct 8, 2023
Hinsdale, IL
Rotary Run Charity Classic
Oct 6, 2024
Evanston, IL
NUDM Sunset 5K
Oct 14, 2023
Waukesha, WI
Bryon's Run/Walk/Roll To Cure Paralysis
Oct 6, 2024
Pleasant Prairie, WI
Scary in the Prairie 5K
Oct 21, 2023
Howl-O-Ween 5K
Oct 29, 2023
Wheaton, IL
Larry St. Onge Memorial Run to Benefit Others
Oct 12, 2024
Hot Cider Hustle
Oct 27, 2024
Oct 26, 2024
Wicked Wine Run
Oct 26, 2024
Saint Charles, IL
Hops for Hope 5K
Oct 5, 2024
Libertyville, IL
Centre Club 5K
Oct 14, 2023
Milwaukee, WI
Run With All Your Heart 5K
Oct 8, 2023
Milwaukee Lakefront Marathon
Oct 6, 2024
Spooky Sprint
Oct 12, 2024
UWM Panther Prowl 5K
Oct 12, 2024
Dia De Los Muertos 5K
Oct 26, 2024
Northbrook, IL
Halloween 3K Run
Oct 20, 2023
Glen Ellyn, IL
This Run's For Jack 5K
Oct 20, 2024
Whitewater, WI
Run for Trey
Oct 8, 2023
Delafield, WI
Lapham Peak Colorama Run
Oct 5, 2024
Elk Grove Village, IL
Butterfly Run
Oct 15, 2023
Crystal Lake, IL
Panting Four Paws Festival 5K/10K
Oct 7, 2023
Fox River Grove, IL
Fox Chase 5K
Oct 1, 2023
Chicago, IL
Bronzeville 5K
Oct 1, 2023
Bucktown 5K
Oct 6, 2024
Head for the Cure 5K
Oct 6, 2024
RBC Race for the Kids
Oct 6, 2024
Chicago 5K
Oct 12, 2024
Chicago Marathon
Oct 13, 2024
Country Sole Half Marathon
Oct 19, 2024
Rosehill Cemetery Crypt 5K
Oct 19, 2024
Wild Blossom Haunted Wine Run 5k
Oct 19, 2024
Will Run for Beer Chicago 5K
Oct 19, 2024
Rise to Shine 10K/5K/1M
Oct 20, 2024
Haunted Halloween Half Marathon
Oct 27, 2024
Illinois Brewery Running Series
Oct 27, 2024
Polish Independence 10K/5K
Oct 27, 2024
Woodstock, IL
Care4 Breast Cancer 5K
Oct 20, 2024
Eagle, WI
Wisconsin Beer Run 5K
Oct 29, 2023
West Chicago, IL
Cornerstone Lakes parkrun
Apr 12, 2025
Apr 19, 2025
Apr 26, 2025
May 3, 2025
48 more
Villa Park, IL
Run for the Kids: Superhero Hustle
Oct 5, 2024
Spring Grove, IL
World's Largest Corn Maze Run & Kids Adventure Run
Oct 6, 2024
Winfield, IL
Winfield Cider Run
Oct 14, 2023
Lake Bluff, IL
Lake Bluff PTO Pumpkin Chase
Oct 28, 2023
Niles, IL
Harvest Hustle 5K
Oct 12, 2024
Sturtevant, WI
Soles for Jesus
Oct 7, 2023
Ingleside, IL
St. Bede School Halloween Hustle
Oct 21, 2023
Shorewood, WI
Hot Cider Hustle
Oct 26, 2024
Muskego, WI
Tri Faster ReRun 5K & 10K
Oct 15, 2023
Wheeling, IL
Day of the Dead 5K
Oct 27, 2024
Rochester, WI
Run for the BooBees
Oct 8, 2023
Darien, WI
Miles for Smiles
Oct 19, 2024
Rolling Meadows, IL
UPAAGC Annual 5K Walk-Run
Oct 7, 2023
Halloween Hot Cocoa & Treats 5K Run/Walk (Schaumburg)
Oct 21, 2023
Truly Lit 5K Series
Oct 21, 2023
Uncorked Wine 5K
Oct 21, 2023
Shannon McNamara Memorial Run
Oct 29, 2023
Howl-O-Ween 5K
Oct 27, 2024
Half Day Forest Preserve, IL
Des Plaines River Trail Races
Oct 12, 2024
Sat | Sun | Mon | Tue | Wed | Thu | Fri | Multiple |
1. Bronzeville 5K
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Past DateOct 1, 2023Sunday
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5K run
More Information
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Chicago, IL
47 miles point to pointCook County, IL
2. Fox Chase 5K
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Past DateOct 1, 2023Sunday
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5K run | kids run
More Information
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Fox River Grove, IL
28 miles point to pointMcHenry County, IL
3. Ted Miller Memorial 5K Run
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Past DateOct 1, 2023Sunday
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5K run
More Information
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Racine, WI
15 miles point to pointRacine County, WI
4. Cornerstone Lakes parkrun
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Oct 5, 2024Saturday
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5K run
More Information
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West Chicago, IL
47 miles point to pointDupage County, IL
5. Hops for Hope 5K
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Oct 5, 2024Saturday
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5K run
More Information
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Saint Charles, IL
48 miles point to pointKane County, IL
6. Lapham Peak Colorama Run
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Oct 5, 2024Saturday
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10K, 5K trail run | kids run
More Information
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Delafield, WI
47 miles point to pointWaukesha County, WI
7. Run for the Kids: Superhero Hustle
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Oct 5, 2024Saturday
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5K run | kids run
More Information
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Villa Park, IL
44 miles point to pointDupage County, IL
8. Bryon's Run/Walk/Roll To Cure Paralysis
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Oct 6, 2024Sunday
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5K run
More Information
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Waukesha, WI
38 miles point to pointWaukesha County, WI
9. Bucktown 5K
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Oct 6, 2024Sunday
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5K run | kids run
More Information
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Chicago, IL
47 miles point to pointCook County, IL
10. Head for the Cure 5K - Chicago
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Oct 6, 2024Sunday
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5K run | kids run
More Information
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Chicago, IL
47 miles point to pointCook County, IL
11. Illinois Brewery Running Series
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Oct 6, 2024Sunday
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5K run
More Information
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Oak Park, IL
44 miles point to pointCook County, IL
12. Lemons of Love Pink Lemonade 5K
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Oct 6, 2024Sunday
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5K run
Virtual OptionMore Information
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Mount Prospect, IL
32 miles point to pointCook County, IL
13. Milwaukee Lakefront Marathon
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Oct 6, 2024Sunday
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26.2M, 13.1M, 5K run | kids run
More Information
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Boston Marathon Qualifier
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Milwaukee, WI
36 miles point to pointMilwaukee County, WI
14. RBC Race for the Kids
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Oct 6, 2024Sunday
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5K run | kids run
More Information
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Chicago, IL
47 miles point to pointCook County, IL
15. Rotary Run Charity Classic
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Oct 6, 2024Sunday
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10K, 5K, 1M run | kids run
More Information
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Hinsdale, IL
50 miles point to pointDupage County, IL
16. World's Largest Corn Maze Run & Kids Adventure Run
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Oct 6, 2024Sunday
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5K, 1M run | kids run
Virtual OptionMore Information
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Spring Grove, IL
19 miles point to pointMcHenry County, IL
17. Panting Four Paws Festival 5K/10K
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Past DateOct 7, 2023Saturday
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10K, 5K run
More Information
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Crystal Lake, IL
30 miles point to pointMcHenry County, IL
18. Soles for Jesus
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Past DateOct 7, 2023Saturday
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5K run
More Information
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Sturtevant, WI
12 miles point to pointRacine County, WI
19. UPAAGC Annual 5K Walk-Run
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Past DateOct 7, 2023Saturday
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5K run
More Information
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Rolling Meadows, IL
31 miles point to pointCook County, IL
20. NSSRA Run for All
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Past DateOct 8, 2023Sunday
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5K, 1M run
More Information
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Glenview, IL
32 miles point to pointCook County, IL
For the love of all that Is good And moisture wicking...
Though we Try To be accurate And On top Of things... Race details can change When we aren't lookin. And once in a while we simply make a mistake.
ALWAYS visit the race's website for the most complete and accurate race information.
ALWAYS visit the race's website for the most complete and accurate race information.