41 Upcoming Races Near Highwood, IL - Matching: Trail Races

Diplo's Run Club Chicago

Chicago, IL

Saturday, October 3rd, 2026

Featured

Code:FTR10

View details for race Diplo's Run Club Chicago

McHenry Lakefront 5K & Kids Fun Run

McHenry, IL

Saturday, July 11th, 2026

Trail

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Disability Awareness Walk, Run, Roll

Evanston, IL

Sunday, July 12th, 2026

Trail

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Highlander Assault Obstacle Race

Mchenry, IL

Saturday, August 15th, 2026

15K

Trail

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Highlander Assault Obstacle Race

Pingree Grove, IL

Saturday, August 15th, 2026

15K

Trail

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Bloom Alumni Cross Country Meet

Chicago Heights, IL

Saturday, August 15th, 2026

Trail

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Run the Rails

Elburn, IL

Saturday, August 22nd, 2026

Trail

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Summer Trail Classic

Hoffman Estates, IL

Sunday, August 23rd, 2026

Code:FTR5

Trail

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Tails on the Trail 5K & 1-Mile Wag & Walk

Matteson, IL

Saturday, August 29th, 2026

1 Mile

Trail

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There Is A Will, There Is A Way 5K

Downers Grove, IL

Saturday, September 5th, 2026

Trail

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Pirate's Booty

St. Charles, IL

Saturday, September 12th, 2026

10K

Trail

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4th Annual Run for the Parks! 5K Run, Walk. or ...

Chicago, IL

Sunday, September 13th, 2026

1 Mile

Trail

View details for race 4th Annual Run for the Parks! 5K Run, Walk. or Roll

St. Veronica 6k Run/Walk for Scholarships

Olympia Fields, IL

Sunday, September 20th, 2026

1 Mile

Trail

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Bloomingdale Trail 5K

Chicago, IL

Saturday, September 26th, 2026

Trail

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District 112 FUNd Run and Family Walk

Highland Park, IL

Saturday, September 26th, 2026

1 Mile

Trail

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Moraine Hills Run for the Hills

McHenry, IL

Saturday, September 26th, 2026

Half

10K

Trail

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Sweet Ride | Bike • Run • Walk

Willow Springs, IL

Saturday, October 3rd, 2026

Trail

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Boo Island - 5K Charity Run/Walk

Blue Island, IL

Saturday, October 3rd, 2026

Trail

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Fire Zone 5k

Lockport, IL

Sunday, October 4th, 2026

Trail

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Zombie Fun Run

Schaumburg, IL

Friday, October 16th, 2026

Trail

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Haunted Highlander Assault Trail Run

Pingree Grove, IL

Friday, October 23rd, 2026

Trail

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Haunted Highlander Assault Trail Run

Mchenry, IL

Friday, October 23rd, 2026

Trail

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Haunted Halloween Half Marathon & 5km

Chicago, IL

Sunday, October 25th, 2026

Half

Trail

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Fast Track Cross Country Open

Schaumburg, IL

Sunday, November 8th, 2026

Trail

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Abominable Trail Race

Lake Geneva, WI

Saturday, November 14th, 2026

10K

15K

Trail

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The Forge Trail Run Festival

Lemont, IL

Saturday, November 14th, 2026

10K

Half

Trail

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Winnetka Turkey Trot 2026

Winnetka, IL

Thursday, November 26th, 2026

Trail

Fast

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Turkey Day 5K (Danada - Naperville)

Naperville, IL

Thursday, November 26th, 2026

Trail

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Resolution Run 6K

Olympia Fields, IL

Friday, January 1st, 2027

Trail

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Fox Valley Winter Challenge Trail Series 5k/8k/10k

Batavia, IL

Saturday, January 23rd, 2027

10K

Trail

Fast

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Fox Valley Winter Challenge Trail Series 5K

Batavia, IL

Saturday, January 23rd, 2027

Trail

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Run for Donut CHICAGO/EVANSTON

Chicago, IL

Saturday, January 30th, 2027

10K

Half

Trail

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Coffee Lover Run CHICAGO/EVANSTON

Chicago, IL

Saturday, January 30th, 2027

10K

Half

Trail

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Abominable Snow Race

Lake Geneva, WI

Saturday, January 30th, 2027

10K

Trail

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Run for Chocolate 5k/10k/13.1 CHICAGO/EVANSTON

Chicago, IL

Saturday, February 13th, 2027

10K

Half

Trail

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Fox Valley Winter Challenge Trail Series 8K

Aurora, IL

Saturday, February 20th, 2027

Trail

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Muddy Shamrock @ The Forge

Lemont, IL

Saturday, March 13th, 2027

Half

10K

Trail

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Fox Valley Winter Challenge Trail Series 10K

St. Charles, IL

Sunday, March 14th, 2027

10K

Trail

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F^3 Cap Sauers Trail Marathon & 10 Mile

Palos Hills, IL

Saturday, May 8th, 2027

Marathon

10 Miles

Trail

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Elgin Valley Fox Trot

Elgin, IL

Sunday, June 6th, 2027

10 Miles

Trail

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Waubonsee Foundation Trail Run

Sugar Grove, IL

Saturday, June 12th, 2027

10K

Trail

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UltraTrax Alpine Valley

Elkhorn, WI

Saturday, October 9th, 2027

1 Mile

Trail

View details for race UltraTrax Alpine Valley

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