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Trail Running Calendar near Lower West Side 2025-2026

Explore the top trail runs near Lower West Side for 2025-2026! We've gathered 128 exciting races in the area. Check out our detailed list below to find your next local race.

May 2026
May
9
Saturday

F^3 Cap Sauers Trail Marathon

Trail Run 10 mi 26 mi
May
9
Saturday

Quarryman Challenge

5 km 10 mi
May
9
Saturday

Pink 5k

5 km
May
17
Sunday

Chicago Spring Half Marathon

10 km 13 mi
May
31
Sunday

North Shore Classic

5 km 13 mi
June 2026
Jun
20
Saturday

1911 Initiative 5k Scholarship Run/Walk

5 km
Jun
27
Saturday

Miles for Maddog

5 km 10 km
July 2026
Jul
4
Saturday

Warrenville Park District Firecracker 5K

5 km
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