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Trail Running Calendar near Near South Side 2025-2026

Explore the top trail runs near Near South Side for 2025-2026! We've gathered 150 exciting races in the area. Check out our detailed list below to find your next local race.

October 2025
Oct
5
Sunday

Chicago 5k

5 km
Oct
5
Sunday

Lemons of Love Pink Lemonade 5K

5 km
Oct
5
Sunday

Run Wild Whittier

5 km
Oct
5
Sunday

Fire Zone 5k

Trail Run 5 km
Oct
11
Saturday

Des Plaines River Trail Races

Trail Run Half Marathon Marathon 50 km 50 mi
Oct
11
Saturday

Larry St. Onge Memorial Run

5 km 10 km
Oct
11
Saturday

Harvest Hustle - Niles

5 km
Oct
11
Saturday

Bolingbrook Howl-O-Ween 5K

5 km
Oct
11
Saturday

West40 Runs

5 km
Oct
12
Sunday

Chicago Marathon

26 mi
Oct
12
Sunday

Wild Blossom Haunted Wine Run 5k

5 km
Oct
18
Saturday

Spooky Sprint - Chicago

5 km 10 km Half Marathon
Oct
18
Saturday

Rosehill Cemetery 'Crypt' 5K

5 km
Oct
18
Saturday

Chicago Fall Classic Half Marathon

10 km Half Marathon
Oct
18
Saturday

The Best Races - Evanston

5 km 10 km 13 mi
Oct
18
Saturday

Palos Park Spooky Shuffle

Trail Run 5 km 10 km
Oct
18
Saturday

Boo Island - 5K Charity Run/Walk

5 km
Oct
18
Saturday

Scary at the Prairie

5 km
Oct
18
Saturday

Cantigny 5K Run/Walk

5 km
Oct
18
Saturday

D91 Dash

5 km
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