Running races in or near Sleepy Hollow, IL
Marathons, 1-milers, 5Ks, half-marathons, 10Ks & more
See below for a frequently-updated, comprehensive list of upcoming running events in the local Sleepy Hollow, IL area. Races listed here include both walking and running events of various distances — from 1-milers, to 5Ks, to marathons, and everything else in between.
2027 Naperville Women's Half Marathon and 5K
Organization: 10xEM LLC
Date of Race: 04-18-2027
Description: The 11th Annual Naperville Women’s Half Marathon 5k ...
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Naperville Women's Half Marathon - Half - Individual
Organization: 10xEM LLC
Date of Race: 04-18-2027
Description: The 11th Annual Naperville Women’s Half Marathon 5k ...
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Waiver - For Children in Jogging Stroller - ...
Organization: 10xEM LLC
Date of Race: 04-18-2027
Description: The 11th Annual Naperville Women’s Half Marathon 5k ...
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Naperville Women's 5K - 5k - Individual
Organization: 10xEM LLC
Date of Race: 04-18-2027
Description: The 11th Annual Naperville Women’s Half Marathon 5k ...
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2026 SKECHERS Wicked Wine Run Chicago
Organization: Wicked Wine Run
Date of Race: 10-24-2026
Description: Whether you’re a seasoned runner or just love to walk and ...
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Harvest Fest Event Sponsor ($100)
Organization: Wildwood Park District
Date of Race: 09-26-2026
Description: Whether you’re a seasoned runner or just love to walk and ...
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6 Week Fall Series Elk Grove Village
Organization: Devine Nutrition Inc.
Date of Race: 10-14-2026
Description: Join us for a 6-week challenge to help All skill ...
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Harvest Fest Beer Tent Sponsor ($250)
Organization: Wildwood Park District
Date of Race: 09-26-2026
Description: Join us for a 6-week challenge to help All skill ...
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OAKtober Walk
Organization: Forest Preserve District of DuPage County
Date of Race: 10-25-2026
Description: DescriptionCelebrate Oak Awareness Month as you enjoy the fall colors and ...
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Zombie Fun Run
Organization: Schaumburg Park District
Date of Race: 10-16-2026
Description: DescriptionRun or walk in your Halloween costume for nearly 2 miles ...
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Chilly Chili 2K
Organization: Schaumburg Park District
Date of Race: 12-05-2026
Description: DescriptionRegister for our 2K here: https://raceroster.com/events/2025/108836/chilly-chili-5k2k Not ready ...
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Chilly Chili Spectator Lunch
Organization: Schaumburg Park District
Date of Race: 12-05-2026
Description: DescriptionWant to cheer on your runner or walker and have lunch ...
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Volunteer then Run! - Individual
Organization: Wicked Wine Run
Date of Race: 10-24-2026
Description: Whether you’re a seasoned runner or just love to walk and ...
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BOTH 5K + 1K! - Individual
Organization: Wicked Wine Run
Date of Race: 10-24-2026
Description: Whether you’re a seasoned runner or just love to walk and ...
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1K WINE WALK - Individual
Organization: Wicked Wine Run
Date of Race: 10-24-2026
Description: Whether you’re a seasoned runner or just love to walk and ...
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5K WICKED WINE RUN - Individual
Organization: Wicked Wine Run
Date of Race: 10-24-2026
Description: Whether you’re a seasoned runner or just love to walk and ...
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6 Week Fall Series- Geneva
Organization: Devine Nutrition Inc.
Date of Race: 10-15-2026
Description: Join us for a 6 week challenge to help you stay ...
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Fall Series- Geneva
Organization: Devine Nutrition Inc.
Date of Race: 10-15-2026
Description: Join us for a 6 week challenge to help you stay ...
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Run to the Pub-elk Grove Village
Organization: Devine Nutrition Inc.
Date of Race: 10-14-2026
Description: Join us for a 6 week challenge to help you stay ...
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Tent or Treat (Vernon Hills)
Organization: Girl Scouts of Greater Chicago & Northwest Indiana
Date of Race: 10-25-2026
Description: Registration will close on Sunday, October 18, 2026 at 11:59 PM.
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Adult Tot Soccer (2-3 yrs)
Organization: Wauconda Park District
Date of Race: 11-07-2026
Description: DescriptionYoung children develop motor skills while having fun running and kicking.
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Adult Tot Soccer (2-3 yrs)
Organization: Wauconda Park District
Date of Race: 10-27-2026
Description: DescriptionYoung children develop motor skills while having fun running and kicking.
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Adult Tot Soccer (2-3 yrs)
Organization: Wauconda Park District
Date of Race: 11-07-2026
Description: DescriptionYoung children develop motor skills while having fun running and kicking.
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Adult Tot Soccer (2-3 yrs)
Organization: Wauconda Park District
Date of Race: 11-07-2026
Description: DescriptionYoung children develop motor skills while having fun running and kicking.
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Adult Tot Soccer (2-3 yrs)
Organization: Wauconda Park District
Date of Race: 10-27-2026
Description: DescriptionYoung children develop motor skills while having fun running and kicking.
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Complete list of running events in and near Sleepy Hollow, IL: Marathons, 1-milers, 5Ks, half-marathons, 10Ks, obstacle courses, walking events & more.
More information about Sleepy Hollow
About Sleepy Hollow
Sleepy Hollow (IL) is a village in Kane County with an estimated population of 3,304.[4]
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Did you know?
In 2014, there were more than 1,100 marathons and more than 541,000 finishers in the U.S.
