Upcoming Races Near Sleepy Hollow, IL in May, 2026

Name: Ruck It 2
Start: 2026-05-24
End: 2026-05-24
Location: Yorkville

The Universal Sole Spring Trail Challenge

Willow Springs, IL

Saturday, May 2nd, 2026

Featured

Trail

View details for race The Universal Sole Spring Trail Challenge

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Empower Run 5k

Libertyville, IL

Saturday, May 2nd, 2026

View details for race Empower Run 5k

Fight Hunger 10K, 5K + 1 Mile Fun Run

Wheaton, IL

Saturday, May 2nd, 2026

10K

1 Mile

View details for race Fight Hunger 10K, 5K + 1 Mile Fun Run

Jacobs Farm Charity Fun Run

Streamwood, IL

Saturday, May 2nd, 2026

View details for race Jacobs Farm Charity Fun Run

Steck Elementary School Fun Run

Aurora, IL

Saturday, May 2nd, 2026

1 Mile

View details for race Steck Elementary School Fun Run

OUTLAST CHICAGO

Palatine, IL

Saturday, May 2nd, 2026

Trail

View details for race OUTLAST CHICAGO

Insight Y.O.B Walk-A-Thon 2026

Berkeley, IL

Saturday, May 2nd, 2026

View details for race Insight Y.O.B Walk-A-Thon 2026

Byron Rocks 5k & 10k - Run it. Walk it. Ruck it.

Byron, IL

Saturday, May 2nd, 2026

10K

View details for race Byron Rocks 5k & 10k - Run it. Walk it. Ruck it.

HOH5K Run/Walk/Roll benefitting the D28 Homer O...

Northbrook, IL

Saturday, May 2nd, 2026

View details for race HOH5K Run/Walk/Roll benefitting the D28 Homer O. Harvey Scholarship Fund

Chicago Empower Walk & 5K Run

Chicago, IL

Saturday, May 2nd, 2026

View details for race Chicago Empower Walk & 5K Run

Chicago Police Memorial Foundation Run to Remember

Chicago, IL

Saturday, May 2nd, 2026

View details for race Chicago Police Memorial Foundation Run to Remember

Hometown Half Marathon & 5k/10k - Greater Chicago

Chicago, IL

Saturday, May 2nd, 2026

1 Mile

10K

View details for race Hometown Half Marathon & 5k/10k - Greater Chicago

Miles for Smiles 5K

Mchenry, IL

Saturday, May 2nd, 2026

View details for race Miles for Smiles 5K

Hanover Township Sprint 2 Spring 5k

Elgin, IL

Saturday, May 2nd, 2026

View details for race Hanover Township Sprint 2 Spring 5k

Historic Highway Hustle - Rt. 66

Joliet, IL

Sunday, May 3rd, 2026

View details for race Historic Highway Hustle - Rt. 66

Run for BEER - Solemn Oath Brewery

Chicago, IL

Sunday, May 3rd, 2026

View details for race Run for BEER - Solemn Oath Brewery

Tailwagger Trot

Lisle, IL

Sunday, May 3rd, 2026

View details for race Tailwagger Trot

Move for MDS 5k - Chicago

Chicago, IL

Sunday, May 3rd, 2026

View details for race Move for MDS 5k - Chicago

Chicagoland Spring Marathon, Half Marathon & 10K

Schaumburg, IL

Sunday, May 3rd, 2026

Marathon

Half

10K

View details for race Chicagoland Spring Marathon, Half Marathon & 10K

Miles for the Military 5k

Lombard, IL

Saturday, May 9th, 2026

1 Mile

View details for race Miles for the Military 5k

F^3 Cap Sauers Trail Marathon & 10 Mile

Palos Hills, IL

Saturday, May 9th, 2026

Marathon

10 Miles

Trail

View details for race F^3 Cap Sauers Trail Marathon & 10 Mile

Ribbons of Hope 5k

New Lenox, IL

Saturday, May 9th, 2026

1 Mile

View details for race Ribbons of Hope 5k

Pink 5k Oak Brook Park District

Oak Brook, IL

Saturday, May 9th, 2026

View details for race Pink 5k Oak Brook Park District

Ribbons of Hope 5k

Mokena, IL

Saturday, May 9th, 2026

1 Mile

View details for race Ribbons of Hope 5k

Mama's Run 2026

Zion, IL

Saturday, May 9th, 2026

View details for race Mama's Run 2026

Stars & Spikes: Totally Rad 5k

Lombard, IL

Saturday, May 9th, 2026

1 Mile

View details for race Stars & Spikes: Totally Rad 5k

La Carrera de las Madres 2026

Chicago, IL

Saturday, May 9th, 2026

View details for race La Carrera de las Madres 2026

Quarryman Challenge

Lemont, IL

Saturday, May 9th, 2026

10 Miles

View details for race Quarryman Challenge

Barrington Mother's Day 5K Run/Walk

Barrington, IL

Sunday, May 10th, 2026

View details for race Barrington Mother's Day 5K Run/Walk

Run for D103 5K Run/Walk

Lincolnshire, IL

Saturday, May 16th, 2026

View details for race Run for D103 5K Run/Walk

Bright Star Community Outreach 5K Run/Walk

Chicago, IL

Saturday, May 16th, 2026

View details for race Bright Star Community Outreach 5K Run/Walk

Wolf Lake 5k

Chicago, IL

Saturday, May 16th, 2026

View details for race Wolf Lake 5k

Family Service Association 5k

Elgin, IL

Saturday, May 16th, 2026

Trail

View details for race Family Service Association 5k

2026 LOGOS MISSIONS RUN FOR LOVE

Glenview, IL

Saturday, May 16th, 2026

View details for race 2026 LOGOS MISSIONS RUN FOR LOVE

BeACTIVE

Joliet, IL

Saturday, May 16th, 2026

View details for race BeACTIVE

2026 Harlem Huskie Hustle 5K Walk/Run & 1 Mile ...

Machesney Park, IL

Saturday, May 16th, 2026

1 Mile

View details for race 2026 Harlem Huskie Hustle 5K Walk/Run & 1 Mile Walk/Run and Kids Fun Run

Spirits Run on the Rocks a Waukegan 5k

Waukegan, IL

Saturday, May 16th, 2026

View details for race Spirits Run on the Rocks a Waukegan 5k

FRC Walk for Life

Zion, IL

Saturday, May 16th, 2026

View details for race FRC Walk for Life

Wheel Run for Meals

Beloit, WI

Saturday, May 16th, 2026

10K

Fast

View details for race Wheel Run for Meals

Wildflower Run

Bristol, WI

Saturday, May 16th, 2026

Trail

View details for race Wildflower Run

Annual Super Hero Shuffle 5k/10k Run/walk

Lake Geneva, WI

Saturday, May 16th, 2026

10K

1 Mile

Trail

View details for race Annual Super Hero Shuffle 5k/10k Run/walk

2026 Willard 5k Fun Run

River Forest, IL

Sunday, May 17th, 2026

View details for race 2026 Willard 5k Fun Run

Darien Dash

Darien, IL

Sunday, May 17th, 2026

10K

1 Mile

View details for race Darien Dash

Kenilworth Memorial Day 5k

Kenilworth, IL

Sunday, May 17th, 2026

View details for race Kenilworth Memorial Day 5k

5k for Hopeful Beginnings

Palatine, IL

Sunday, May 17th, 2026

View details for race 5k for Hopeful Beginnings

Dash for the Dogs 13th Annual 5K Run/Walk

Barrington, IL

Sunday, May 17th, 2026

1 Mile

View details for race Dash for the Dogs 13th Annual 5K Run/Walk

5th Annual Falcons Walk for Wellness

Fontana, WI

Friday, May 22nd, 2026

Trail

View details for race 5th Annual Falcons Walk for Wellness

Western Springs Tower Trot

Western Springs, IL

Saturday, May 23rd, 2026

10K

Ultra

View details for race Western Springs Tower Trot

Frontline OCR

Byron, IL

Saturday, May 23rd, 2026

10K

1 Mile

View details for race Frontline OCR

Ruck It 2

Yorkville, IL

Sunday, May 24th, 2026

View details for race Ruck It 2

Explore more in Sleepy Hollow, IL

Distances:

5K 10K Half Marathon Marathon

Months:

April May June

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Illinois races

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