Illinois Trail Running Calendar 2025-2026

Header image

Explore the best trail runs in Illinois for 2025-2026! Our updated list features 345 exciting races across the region. Find your next race in Illinois below and join the running community at these great events!

September 2025
Sep
13
Saturday

Wild Wild Wilderness

Trail Run 5 km 7 km
Sep
13
Saturday

Monster 5K Run/Walk

3 km 5 km
Sep
13
Saturday

Friends of the Poor Walk and Run

3 mi
Sep
13
Saturday

The Best Races - Evanston

5 km 10 km 13 mi
Sep
13
Saturday

The Best Races - Chicago Loop

5 km 10 km 13 mi
Sep
14
Sunday

Timely Nonsense - Chicago, IL

Backyard Ultra 6 hr 12 hr
Sep
14
Sunday

Big Horse 5K

Trail Run 5 km
Sep
14
Sunday

El Grito Family Run/Walk

5 km
Sep
14
Sunday

Tyler 'Smitty' Smith 5K

5 km
Sep
20
Saturday

Harvest Hammer Duathlon

Duathlon
Sep
20
Saturday

Tiger 10 Miler

Trail Run 10 mi
Sep
20
Saturday

Operation Obstacle

Obstacle Run 2 mi
Sep
20
Saturday

4sta Hike

Trail Run
Sep
20
Saturday

Half Day at the Lake

Trail Run 6 hr 12 hr
Sep
20
Saturday

Run for the STARS 5k

5 km
Sep
21
Sunday

Carlyle Lake Triathlon

Triathlon
Sep
21
Sunday

St. Veronica 6k Run/Walk for Scholarships

6 km
Sep
21
Sunday

Fox Valley Marathon Races

5 km 13 mi 20 mi 26 mi
Sep
26
Friday

Run for Hope - Vienna, IL

5 km 10 km
Sep
27
Saturday

Midwest OCR

Obstacle Run 5 km 10 km
Articles
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series
Stride with Confidence: A Comprehensive Guide to Saucony Running Shoes