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Trail Running Calendar near Wheeling 2025-2026

Explore the top trail runs near Wheeling for 2025-2026! We've gathered 34 exciting races in the area. Check out our detailed list below to find your next local race.

September 2025
Sep
6
Saturday

Last Chance BQ.2 Marathon

26 mi
Sep
6
Saturday

Naperville Trails Half Marathon

Trail Run 10 km 13 mi
Sep
13
Saturday

Monster 5K Run/Walk

3 km 5 km
Sep
13
Saturday

Friends of the Poor Walk and Run

Sep
14
Sunday

Timely Nonsense - Chicago, IL

Backyard Ultra 6 hr 12 hr
Sep
14
Sunday

El Grito Family Run/Walk

5 km
Sep
21
Sunday

Fox Valley Marathon Races

5 km 13 mi 20 mi 26 mi
Sep
27
Saturday

Lawndale 5K

5 km
Sep
28
Sunday

Lester Fun Run

5 km
Sep
28
Sunday

Chicago Half Marathon

5 km 13 mi
October 2025
Oct
4
Saturday

Scarecrow Scramble

5 km
Oct
4
Saturday

Long Grove's Prairie State Half Marathon

5 km 10 km 13 mi
Oct
5
Sunday

Bronzeville 5K

5 km
Oct
5
Sunday

Chicago 5k

5 km
Oct
11
Saturday

Des Plaines River Trail Races

Trail Run 13 mi 26 mi 50 km 50 mi
Oct
12
Sunday

Chicago Marathon

Oct
18
Saturday

Spooky Sprint - Chicago

5 km 10 km 13 mi
Oct
18
Saturday

Rosehill Cemetery 'Crypt' 5K

5 km
Oct
18
Saturday

Country Sole Half Marathon

5 km 10 km 13 mi
Oct
19
Sunday

Naperville Half Marathon

5 km 10 km 13 mi
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