34 Upcoming Races Near Sycamore, 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

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

Highlander Assault Obstacle Race

Pingree Grove, IL

Saturday, August 15th, 2026

15K

Trail

View details for race Highlander Assault Obstacle Race

Highlander Assault Obstacle Race

Mchenry, IL

Saturday, August 15th, 2026

15K

Trail

View details for race Highlander Assault Obstacle Race

Organize a race? Add it free — over 100,000 runners use Find The Run every month.

Add it free Feature it

Run the Rails

Elburn, IL

Saturday, August 22nd, 2026

Trail

View details for race Run the Rails

Summer Trail Classic

Hoffman Estates, IL

Sunday, August 23rd, 2026

Code:FTR5

Trail

View details for race Summer Trail Classic

There Is A Will, There Is A Way 5K

Downers Grove, IL

Saturday, September 5th, 2026

Trail

View details for race There Is A Will, There Is A Way 5K

Hobo Trail Runs 10k-25k-50k

Rockford, IL

Friday, September 11th, 2026

Ultra

10K

Trail

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

Pirate's Booty

St. Charles, IL

Saturday, September 12th, 2026

10K

Trail

View details for race Pirate's Booty

Tiger 10 Miler - 9th Annual Trail Race Presente...

Byron, IL

Saturday, September 19th, 2026

10 Miles

Trail

View details for race Tiger 10 Miler - 9th Annual Trail Race Presented by Byron Bank

Stone Bridge Half Marathon and 5k

Roscoe, IL

Saturday, September 26th, 2026

Half

Trail

Fast

View details for race Stone Bridge Half Marathon and 5k

Moraine Hills Run for the Hills

McHenry, IL

Saturday, September 26th, 2026

Half

10K

Trail

View details for race Moraine Hills Run for the Hills

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

Sweet Ride | Bike • Run • Walk

Willow Springs, IL

Saturday, October 3rd, 2026

Trail

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

Fire Zone 5k

Lockport, IL

Sunday, October 4th, 2026

Trail

View details for race Fire Zone 5k

Zombie Fun Run

Schaumburg, IL

Friday, October 16th, 2026

Trail

View details for race Zombie Fun Run

Saw Wee Kee - Fall Trail Run

Yorkville, IL

Saturday, October 17th, 2026

Trail

View details for race Saw Wee Kee - Fall Trail Run

JAIMIE COX MEMORIAL RUN

Roscoe, IL

Saturday, October 17th, 2026

Trail

View details for race JAIMIE COX MEMORIAL RUN

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

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

The Forge Trail Run Festival

Lemont, IL

Saturday, November 14th, 2026

10K

Half

Trail

View details for race The Forge Trail Run Festival

Turkey Day 5K (Danada - Naperville)

Naperville, IL

Thursday, November 26th, 2026

Trail

View details for race Turkey Day 5K (Danada - Naperville)

Winnetka Turkey Trot 2025

Winnetka, IL

Thursday, November 26th, 2026

Trail

Fast

View details for race Winnetka Turkey Trot 2025

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

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

Batavia, IL

Saturday, January 23rd, 2027

10K

Trail

Fast

View details for race Fox Valley Winter Challenge Trail Series 5k/8k/10k

Abominable Snow Race

Lake Geneva, WI

Saturday, January 30th, 2027

10K

Trail

View details for race Abominable Snow Race

Fox Valley Winter Challenge Trail Series 8K

Aurora, IL

Saturday, February 20th, 2027

Trail

View details for race Fox Valley Winter Challenge Trail Series 8K

Muddy Shamrock @ The Forge

Lemont, IL

Saturday, March 13th, 2027

Half

10K

Trail

View details for race Muddy Shamrock @ The Forge

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

F^3 Cap Sauers Trail Marathon & 10 Mile

Palos Hills, IL

Saturday, May 8th, 2027

Marathon

10 Miles

Trail

View details for race F^3 Cap Sauers Trail Marathon & 10 Mile

Elgin Valley Fox Trot

Elgin, IL

Sunday, June 6th, 2027

10 Miles

Trail

View details for race Elgin Valley Fox Trot

Waubonsee Foundation Trail Run

Sugar Grove, IL

Saturday, June 12th, 2027

10K

Trail

View details for race Waubonsee Foundation Trail Run

UltraTrax Alpine Valley

Elkhorn, WI

Saturday, October 9th, 2027

1 Mile

Trail

View details for race UltraTrax Alpine Valley

Explore more in Sycamore, IL

Jump straight to races by distance, month, or type.

Distance

5K 10K Half Marathon Marathon

Month

July August September

Race type

Trail Boston Qualifiers Fast Courses

Run clubs

Run clubs in Sycamore

Nearby

Elburn Elgin St. Charles Geneva Batavia Crystal Lake All Illinois races