Upcoming Races Near Mchenry, IL - Matching: Trail Races

Name: Wisconsin Pickle Run
Start: 2026-05-17
End: 2026-05-17
Location: Wales

Featured Races Get Seen

Be the first race runners see — and grow your registrations. Put your race at the top.

Feature Your Race

Learn how to feature your race

Hobo Trail Runs 10k-25k-50k

Rockford, IL

Friday, September 12th, 2025

Ultra

10K

Trail

View details for race Hobo Trail Runs 10k-25k-50k

DoLittle Marathon

Waukesha, WI

Saturday, September 13th, 2025

Marathon

Half

10K

Trail

Fast

View details for race DoLittle Marathon

National Chocolate Day: Run for Chocolates CHIC...

Chicago, IL

Saturday, September 13th, 2025

10K

Half

Trail

View details for race National Chocolate Day: Run for Chocolates CHICAGO/EVANSTON

3rd Annual Run for the Parks! 5K Run, Walk or Roll

Chicago, IL

Sunday, September 14th, 2025

1 Mile

Trail

View details for race 3rd Annual Run for the Parks! 5K Run, Walk or Roll

Procrastination Run

Waukesha, WI

Saturday, September 20th, 2025

Half

10K

Trail

View details for race Procrastination Run

Bloomingdale Trail 5K

Chicago, IL

Saturday, September 27th, 2025

Trail

View details for race Bloomingdale Trail 5K

National Coffee Day: Run for Coffee CHICAGO/EVA...

Chicago, IL

Saturday, September 27th, 2025

10K

Half

Trail

View details for race National Coffee Day: Run for Coffee CHICAGO/EVANSTON

National Singles Day: Singles & Friends Running...

Chicago, IL

Saturday, September 27th, 2025

10K

Half

Trail

View details for race National Singles Day: Singles & Friends Running Club CHICAGO/EVANSTON

District 112 FUNd Run and Family Walk

Highland Park, IL

Saturday, September 27th, 2025

1 Mile

Trail

View details for race District 112 FUNd Run and Family Walk

Stone Bridge Half Marathon and 5k

Roscoe, IL

Saturday, September 27th, 2025

Half

Trail

Fast

View details for race Stone Bridge Half Marathon and 5k

Fall Color Festival

Whitewater, WI

Saturday, September 27th, 2025

Ultra

Half

1 Mile

Trail

View details for race Fall Color Festival

Sweet Ride | Bike • Run • Walk

Willow Springs, IL

Saturday, October 4th, 2025

Trail

View details for race Sweet Ride | Bike • Run • Walk

Fall Trail Classic 2.0

Marengo, IL

Saturday, October 4th, 2025

1 Mile

Trail

View details for race Fall Trail Classic 2.0

Farmer Ken's Pumpkin Dash 5K

Franksville, WI

Sunday, October 5th, 2025

Trail

View details for race Farmer Ken's Pumpkin Dash 5K

Larry St. Onge Memorial Run to Benefit Others

Wheaton, IL

Saturday, October 11th, 2025

10K

Trail

View details for race Larry St. Onge Memorial Run to Benefit Others

JAIMIE COX MEMORIAL RUN

Roscoe, IL

Saturday, October 18th, 2025

Trail

View details for race JAIMIE COX MEMORIAL RUN

22nd Annual This Run's For Jack 2025

Glen Ellyn, IL

Sunday, October 19th, 2025

Trail

View details for race 22nd Annual This Run's For Jack 2025

Among the Trees

Dousman, WI

Saturday, October 25th, 2025

Ultra

Trail

View details for race Among the Trees

Haunted Halloween Half Marathon & 5km

Chicago, IL

Sunday, October 26th, 2025

Half

Trail

View details for race Haunted Halloween Half Marathon & 5km

Bristol Woods Trail Run

Bristol, WI

Saturday, November 1st, 2025

Trail

View details for race Bristol Woods Trail Run

Warrior 5K & 8K...Through The Park

West Allis, WI

Saturday, November 8th, 2025

Trail

View details for race Warrior 5K & 8K...Through The Park

Fast Track Cross Country Open

Schaumburg, IL

Sunday, November 9th, 2025

Trail

Fast

View details for race Fast Track Cross Country Open

The Forge Trail Run Festival

Lemont, IL

Saturday, November 15th, 2025

10K

Half

Trail

View details for race The Forge Trail Run Festival

Abominable Trail Race

Lake Geneva, WI

Saturday, November 15th, 2025

15K

Ultra

Trail

View details for race Abominable Trail Race

Winnetka Turkey Trot 2025

Winnetka, IL

Thursday, November 27th, 2025

Trail

Fast

View details for race Winnetka Turkey Trot 2025

Abominable Snow Race

Lake Geneva, WI

Saturday, January 31st, 2026

10K

Trail

View details for race Abominable Snow Race

Muddy Shamrock @ The Forge

Lemont, IL

Saturday, March 14th, 2026

Half

10K

Trail

View details for race Muddy Shamrock @ The Forge

First Call 5K, 10K, & 1/2 Marathon

Waukesha, WI

Sunday, March 22nd, 2026

10K

Half

Trail

Fast

View details for race First Call 5K, 10K, & 1/2 Marathon

Trailbreaker

Waukesha, WI

Sunday, March 29th, 2026

Marathon

Half

10K

Trail

View details for race Trailbreaker

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

Wisconsin Pickle Run

Wales, WI

Sunday, May 17th, 2026

Trail

View details for race Wisconsin Pickle Run

Explore more in Mchenry, IL

Distances:

5K 10K Half Marathon Marathon

Months:

August September October

Tags:

Trail Boston Qualifiers Fast Courses

State:

All Illinois races

Don't see your race? Add it!

Add Your Race (Free)