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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.

May 2026
May
31
Sunday

North Shore Classic

5 km Half Marathon
June 2026
Jun
7
Sunday

Leon's Triathlon

Triathlon
Jun
20
Saturday

1911 Initiative 5k Scholarship Run/Walk

5 km
Jun
20
Saturday

Love's Fox Trot 5K

5 km
Jun
27
Saturday

Miles for Maddog

5 km 10 km
Jun
27
Saturday

Run the Runway - Wheeling

5 km
July 2026
Jul
4
Saturday

Warrenville Park District Firecracker 5K

5 km
August 2026
Aug
1
Saturday

College of DuPage Alumni 5k

5 km
September 2026
Sep
19
Saturday

HBCU Run & Brunch

5 km 10 km
October 2026
Oct
4
Sunday

Chicago 10K

10 km
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