Upcoming 5K Races Near Sleepy Hollow, IL

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Haunted Halloween Half Marathon & 5km

Chicago, IL

Sunday, October 25th, 2026

Half

Trail

View details for race Haunted Halloween Half Marathon & 5km

Fraidycat 5k,8k & Meow Mile

Oswego, IL

Sunday, October 25th, 2026

1 Mile

View details for race Fraidycat 5k,8k & Meow Mile

Spooky Sprint - Greater Chicago

Shorewood, IL

Sunday, October 25th, 2026

1 Mile

10K

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Spooky Sprint - Greater Chicago

Greater Chicago, IL

Sunday, October 25th, 2026

1 Mile

10K

View details for race Spooky Sprint - Greater Chicago

Howl-o-ween 5k - Dan Ryan Woods

Chicago, IL

Sunday, October 25th, 2026

View details for race Howl-o-ween 5k - Dan Ryan Woods

Haunted Oak 5K

Homer Glen, IL

Sunday, October 25th, 2026

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Hot Cider Hustle - Wheaton 8 Mile Run & 5K Run/...

Wheaton, IL

Sunday, October 25th, 2026

View details for race Hot Cider Hustle - Wheaton 8 Mile Run & 5K Run/Walk

St. Francis Xavier Falcon 5K Run/Walk

La Grange Park, IL

Saturday, November 7th, 2026

View details for race St. Francis Xavier Falcon 5K Run/Walk

2026 Jingle Bell Run - Western Suburbs, IL

Wheaton, IL

Saturday, November 14th, 2026

1 Mile

View details for race 2026 Jingle Bell Run - Western Suburbs, IL

Abominable Trail Race

Lake Geneva, WI

Saturday, November 14th, 2026

10K

15K

Trail

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Lisle Turkey Trot Tune-Up 5K

Lisle, IL

Sunday, November 15th, 2026

View details for race Lisle Turkey Trot Tune-Up 5K

Grayslake Central Turkey Trot

Grayslake, IL

Sunday, November 15th, 2026

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Tom-A-Hawk Turkey Trot 5k

Aurora, IL

Saturday, November 21st, 2026

Fast

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Run with the Turkeys 5K

Pleasant Prairie, WI

Saturday, November 21st, 2026

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Lincolnwood Turkey Trot: 5K, 10K, Walk, Dash

Lincolnwood, IL

Sunday, November 22nd, 2026

10K

View details for race Lincolnwood Turkey Trot: 5K, 10K, Walk, Dash

The Great Turkey Chase: Wolfpack 5K

Crystal Lake, IL

Sunday, November 22nd, 2026

View details for race The Great Turkey Chase: Wolfpack 5K

St. Charles Turkey Trot 5K

St. Charles, IL

Thursday, November 26th, 2026

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McHenry Kiwanis Club's Turkey Trot 5K

McHenry, IL

Thursday, November 26th, 2026

View details for race McHenry Kiwanis Club's Turkey Trot 5K

Chi Town Turkey Trot 5K & 10K

Chicago, IL

Thursday, November 26th, 2026

10K

View details for race Chi Town Turkey Trot 5K & 10K

Grove Express 5K

Downers Grove, IL

Thursday, November 26th, 2026

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Long Grove Turkey Trot 5K & 8K

Long Grove, IL

Thursday, November 26th, 2026

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Winnetka Turkey Trot 2026

Winnetka, IL

Thursday, November 26th, 2026

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5k Turkey Trot Family Tradition 2026

Elmwood Park, IL

Thursday, November 26th, 2026

1 Mile

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Turkey Trails - Greater Chicago

Greater Chicago, IL

Saturday, November 28th, 2026

1 Mile

10K

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Schaumburg Turkey Trot Half Marathon & 5K

Elk Grove Village, IL

Saturday, November 28th, 2026

Half

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Turkey Trails - Greater Chicago

Shorewood, IL

Saturday, November 28th, 2026

1 Mile

10K

View details for race Turkey Trails - Greater Chicago

The Village of Norridge 5K Reindeer Run and Kid...

Norridge, IL

Saturday, December 5th, 2026

View details for race The Village of Norridge 5K Reindeer Run and Kids Dash

Santa Hustle Chicago

Chicago, IL

Saturday, December 5th, 2026

10K

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Rotary Santa Run Walk & Reindeer Dash

Arlington Heights, IL

Saturday, December 5th, 2026

View details for race Rotary Santa Run Walk & Reindeer Dash

Santa's Run through the Lights 5K Run/Walk

Geneva, IL

Saturday, December 5th, 2026

View details for race Santa's Run through the Lights 5K Run/Walk

Reindeer Run 5K 2026

Wheaton, IL

Saturday, December 5th, 2026

View details for race Reindeer Run 5K 2026

Lemont Frigid 5K

Lemont, IL

Sunday, December 6th, 2026

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Park Ridge Santa Stroll 5k - Stroll Mile - Jing...

Park Ridge, IL

Saturday, December 12th, 2026

1 Mile

View details for race Park Ridge Santa Stroll 5k - Stroll Mile - Jingle Jog

Candy Cane Course- Greater Chicago

Greater Chicago, IL

Saturday, December 12th, 2026

1 Mile

10K

View details for race Candy Cane Course- Greater Chicago

Candy Cane Course- Greater Chicago

Elk Grove Village, IL

Saturday, December 12th, 2026

1 Mile

10K

View details for race Candy Cane Course- Greater Chicago

2026 Jingle Bell Run - Chicago, IL

Chicago, IL

Saturday, December 12th, 2026

1 Mile

View details for race 2026 Jingle Bell Run - Chicago, IL

Catch the Elf 5k & 10k

Markham, IL

Saturday, December 19th, 2026

10K

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Cheers to New Year's 5k Run/Walk

Itasca, IL

Friday, January 1st, 2027

View details for race Cheers to New Year's 5k Run/Walk

Fox Valley Winter Challenge Trail Series 5K

Batavia, IL

Saturday, January 23rd, 2027

Trail

View details for race Fox Valley Winter Challenge Trail Series 5K

18th Annual F^3 Lake Half Marathon & 5k

Chicago, IL

Saturday, January 30th, 2027

Half

View details for race 18th Annual F^3 Lake Half Marathon & 5k

Abominable Snow Race

Lake Geneva, WI

Saturday, January 30th, 2027

10K

Trail

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Manhattan Irish Fest Parade 5k

Manhattan, IL

Saturday, March 6th, 2027

Fast

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Shorewood Shuffle

Shorewood, IL

Saturday, March 13th, 2027

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Welcome to the 11th Annual SOB Run

Yorkville, IL

Saturday, March 13th, 2027

View details for race Welcome to the 11th Annual SOB Run

Footsteps for Families: 5k, Walk & Kids Run

Machesney Park, IL

Saturday, April 10th, 2027

1 Mile

View details for race Footsteps for Families: 5k, Walk & Kids Run

2027 Naperville Women's Half Marathon and 5K

Naperville, IL

Sunday, April 18th, 2027

Half

View details for race 2027 Naperville Women's Half Marathon and 5K

I Raced The Law 5K and Color Run

Oswego, IL

Sunday, April 18th, 2027

1 Mile

View details for race I Raced The Law 5K and Color Run

Ravenswood Run presented by Fleet Feet x Altra

Chicago, IL

Sunday, April 25th, 2027

View details for race Ravenswood Run presented by Fleet Feet x Altra

Good Life Race

Oak Park, IL

Sunday, April 25th, 2027

1 Mile

Fast

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

Byron, IL

Saturday, May 1st, 2027

10K

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

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