30 Upcoming Races Near Pleasant Prairie, WI - Matching: Trail Races

McHenry Lakefront 5K & Kids Fun Run

McHenry, IL

Saturday, July 11th, 2026

Trail

View details for race McHenry Lakefront 5K & Kids Fun Run

Disability Awareness Walk, Run, Roll

Evanston, IL

Sunday, July 12th, 2026

Trail

View details for race Disability Awareness Walk, Run, Roll

Cudahy Classic

Cudahy, WI

Saturday, July 25th, 2026

10 Miles

1 Mile

Trail

Fast

View details for race Cudahy Classic

Casual Hikers 10k Walk/Run

Whitewater, WI

Saturday, August 1st, 2026

10K

Trail

View details for race Casual Hikers 10k Walk/Run

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26th Annual Hank Aaron State Trail 5K Run/Walk

Milwaukee, WI

Saturday, August 8th, 2026

Trail

Fast

View details for race 26th Annual Hank Aaron State Trail 5K Run/Walk

Highlander Assault Obstacle Race

Mchenry, IL

Saturday, August 15th, 2026

15K

Trail

View details for race Highlander Assault Obstacle Race

Highlander Assault Obstacle Race

Pingree Grove, IL

Saturday, August 15th, 2026

15K

Trail

View details for race Highlander Assault Obstacle Race

Labor Day 5K - Elm Grove, WI - 2026

Elm Grove, WI

Saturday, September 5th, 2026

Trail

View details for race Labor Day 5K - Elm Grove, WI - 2026

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

Fall Color Festival

Whitewater, WI

Saturday, September 26th, 2026

Ultra

Half

1 Mile

Trail

View details for race Fall Color Festival

Bloomingdale Trail 5K

Chicago, IL

Saturday, September 26th, 2026

Trail

View details for race Bloomingdale Trail 5K

District 112 FUNd Run and Family Walk

Highland Park, IL

Saturday, September 26th, 2026

1 Mile

Trail

View details for race District 112 FUNd Run and Family Walk

Christmas Clearing Council Jingle Bell Jog and ...

Pewaukee, WI

Saturday, September 26th, 2026

Trail

View details for race Christmas Clearing Council Jingle Bell Jog and Walk

Talk Pirate to Me 5K/10K/Half - Milwaukee

Glendale, WI

Sunday, September 27th, 2026

10K

Half

Trail

View details for race Talk Pirate to Me 5K/10K/Half - Milwaukee

Lapham Peak Colorama Run/Walk

Delafield, WI

Saturday, October 3rd, 2026

10K

Trail

View details for race Lapham Peak Colorama Run/Walk

The Milwaukee Beer Run 5k & .05k

Glendale, WI

Sunday, October 4th, 2026

Trail

View details for race The Milwaukee Beer Run 5k & .05k

National Sweetest Day

Nashotah, WI

Saturday, October 17th, 2026

Half

10K

Trail

View details for race National Sweetest Day

Haunted Highlander Assault Trail Run

Pingree Grove, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Haunted Highlander Assault Trail Run

Mchenry, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Haunted Halloween Half Marathon & 5km

Chicago, IL

Sunday, October 25th, 2026

Half

Trail

View details for race Haunted Halloween Half Marathon & 5km

Among the Trees

Dousman, WI

Saturday, October 31st, 2026

Ultra

Trail

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Fast Track Cross Country Open

Schaumburg, IL

Sunday, November 8th, 2026

Trail

View details for race Fast Track Cross Country Open

Abominable Trail Race

Lake Geneva, WI

Saturday, November 14th, 2026

10K

15K

Trail

View details for race Abominable Trail Race

Winnetka Turkey Trot 2025

Winnetka, IL

Thursday, November 26th, 2026

Trail

Fast

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Coffee Lover Run CHICAGO/EVANSTON

Chicago, IL

Saturday, January 30th, 2027

10K

Half

Trail

View details for race Coffee Lover Run CHICAGO/EVANSTON

Abominable Snow Race

Lake Geneva, WI

Saturday, January 30th, 2027

10K

Trail

View details for race Abominable Snow Race

ARKTOS

Dousman, WI

Saturday, February 27th, 2027

Trail

View details for race ARKTOS

Fox Valley Winter Challenge Trail Series 10K

St. Charles, IL

Sunday, March 14th, 2027

10K

Trail

View details for race Fox Valley Winter Challenge Trail Series 10K

Elgin Valley Fox Trot

Elgin, IL

Sunday, June 6th, 2027

10 Miles

Trail

View details for race Elgin Valley Fox Trot

UltraTrax Alpine Valley

Elkhorn, WI

Saturday, October 9th, 2027

1 Mile

Trail

View details for race UltraTrax Alpine Valley

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Nearby

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