27 Upcoming Races Near Waukesha County, WI - Matching: Trail Races

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14th Annual Outrun the Cops 5K Run/Walk

Gurnee, IL

Saturday, June 27th, 2026

10K

Trail

View details for race 14th Annual Outrun the Cops 5K Run/Walk

Lake Country Freedom 5K, 10K & 25K

Oconomowoc, WI

Saturday, July 4th, 2026

10K

Trail

Fast

View details for race Lake Country Freedom 5K, 10K & 25K

McHenry Lakefront 5K & Kids Fun Run

McHenry, IL

Saturday, July 11th, 2026

Trail

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

Headbanger Half

Oconomowoc, WI

Sunday, July 12th, 2026

Half

10K

Trail

Fast

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Cudahy Classic

Cudahy, WI

Saturday, July 25th, 2026

10 Miles

1 Mile

Trail

Fast

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National Watermelon Day Run

Hartford, WI

Saturday, August 1st, 2026

Half

10K

Trail

View details for race National Watermelon Day Run

Casual Hikers 10k Walk/Run

Whitewater, WI

Saturday, August 1st, 2026

10K

Trail

View details for race Casual Hikers 10k Walk/Run

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

Slinger Kiwanis Heads UP 5K Run/Walk

Slinger, WI

Saturday, August 22nd, 2026

Trail

View details for race Slinger Kiwanis Heads UP 5K Run/Walk

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

DoLittle Marathon

Oconomowoc, WI

Saturday, September 12th, 2026

Marathon

Half

10K

Trail

Fast

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Adrenaline Races

West Bend, WI

Sunday, September 20th, 2026

Marathon

Half

10K

Trail

View details for race Adrenaline Races

Fall Color Festival

Whitewater, WI

Saturday, September 26th, 2026

Ultra

Half

1 Mile

Trail

View details for race Fall Color Festival

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

Monday, September 28th, 2026

10K

Half

Trail

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

Fall into Fall Trail 5k

Janesville, WI

Saturday, October 3rd, 2026

Trail

View details for race Fall into Fall Trail 5k

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

Race For Open Space

West Bend, WI

Sunday, October 11th, 2026

10K

1 Mile

Trail

View details for race Race For Open Space

National Sweetest Day

Nashotah, WI

Saturday, October 17th, 2026

Half

10K

Trail

View details for race National Sweetest Day

Haunted Highlander Assault Trail Run

Mchenry, IL

Friday, October 23rd, 2026

Trail

View details for race Haunted Highlander Assault Trail Run

Among the Trees

Dousman, WI

Saturday, October 31st, 2026

Ultra

Trail

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Abominable Trail Race

Lake Geneva, WI

Saturday, November 14th, 2026

10K

15K

Trail

View details for race Abominable Trail Race

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

UltraTrax Alpine Valley

Elkhorn, WI

Saturday, October 9th, 2027

1 Mile

Trail

View details for race UltraTrax Alpine Valley

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